Best Doug Miles Podcasts (2025)

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Episode 199: "On the Town with Suz and Doug" Review Breakfast at McDonalds 4:00

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4d ago4:00

4:00

"On the Town with Suz and Doug" Review Breakfast at McDonalds in Sarasota, FL. Is it still good? Note: We are not comped for our meals. (dougmilesmedia)

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On The Cusp Of Early Retirement: I Leave My W-2 In 4 Months | MHFI 286 57:20

2h ago57:20

57:20

Doug chats with Brad Finley who is on the cusp of early retirement. Brad discusses the decision to leave his W-2 job, steps he’s taking to prepare for the transition, the emotional journey that accompanies such a significant life change, and his plans to maintain a balanced & fulfilling lifestyle post-retirement. Brad also shares his transformative…

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1974 Ford Mustang II Coupe First Car - Jeremy - From Mustangs to Million-Dollar Ideas 35:41

17h ago35:41

35:41

Click here to share your favorite car, car story or any automotive trivia! Jeremy's automotive story began with at age 14, when his dad purchased a 1974 Ford Mustang II coupe for a father-son project. This malaise-era Mustang became his introduction to both driving and wrenching, setting him on a path that would lead to becoming an ASE-certified me…

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AI Public Relations: Building Trust, Not Just Links with Chris Panteli and Nick Biggs 31:28

2h ago31:28

31:28

Send us a text In this episode of the Human-First AI Marketing® podcast, we’re joined by Chris Panteli and Nick Biggs, founders of Linkifi, to talk about how digital PR is evolving in a world dominated by AI, LLMs, and search engines that think like humans. We unpack what white hat link building actually looks like in 2025, why traditional press re…

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Miles Jupp on JL Carr, author of A Month in the Country 27:28

7m ago27:28

27:28

"I find his novels extraordinarily beautiful .. and they're an excellent length." Miles Jupp picks an author he loves, but knows little about. JL Carr was born in Yorkshire and was a teacher, mapmaker, and an eccentric. Joining the comedian in studio to discuss Carr is a man who knew him well - DJ Taylor - who paints a picture of a man who hated Lo…

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20VC: General Catalyst CEO Hemant Taneja on The Future of Venture Capital: Chanel vs Walmart | Lessons Scaling GC to $40BN in AUM | Investing $5BN+ Into Stripe Over 14 Rounds | Investing Hundreds of Millions ... 1:27:19

1d ago1:27:19

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Hemant Taneja is the CEO and leader of General Catalyst, the firm he has scaled over the last decade into one of the largest with over $40BN in AUM. He has been one of the most influential investors of the past two decades, leading early bets in Stripe, Snap, Gusto, Samsara, Grammarly, and Canva. He also played a pivotal role in Livongo’s $18.5B me…

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20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War ... 59:59

5d ago59:59

59:59

Jesse Zhang is the Co-Founder and CEO @ Decagon, the conversational AI platform for customer experience. As one of the fastest growing companies in the valley, they have raised over $230M at a last round price of $1.5BN. Prior to Decagon, Jesse founded Lowkey (acquired by Niantic), studied CS at Harvard, and worked at places like Google, HRT, Citad…

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#271: A Stand Firm Mailbag: Charlie Kirk and Questioning a Pastoral Candidate 49:04

2h ago49:04

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Matt, Jady, and Nick dip into the mailbag, answering questions about the Charlie Kirk assassination, a preacher's obligation (or not) to engage current socio-political events, and what questions a vestry should ask a candidate for pastoral ministry.By Stand Firm

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Human and Machine Learning: Coaching Sales Teams with Causal AIwith Owen Lawlor 33:02

3h ago33:02

33:02

Send us a text In this episode of the Human-First AI Marketing® podcast, Mike Montague sits down with Owen Lawlor, VP of AI at CoachEm, to explore how AI can be used with humans, not against them. You’ll hear how CoachEm is helping sales leaders move beyond dashboards and activity metrics by using causal AI and machine learning to uncover why perfo…

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Maximizing Agency Credibility with Physical Locations and Reputation Management Services | EP 6 30:26

1d ago30:26

30:26

Curious if you should go 100% remote or have physical locations? Unsure how much emphasis should be put on Google reviews and staff training? Reputation management, the impact of physical locations on agency credibility and visibility, and the broad skill set (and constant improvement of those skills) required of agency owners are all pillars of di…

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20VC: Opendoor's CEO on The Greatest Turnaround in Tech | OpenAI and Oracle: How Can Either Afford to Do This | How Anthropic Could Lose 50% of Their Revenue Overnight | Replit Raises at $3BN | Figure ... 1:24:20

6d ago1:24:20

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AGENDA: 00:00 Opendoor's Potential and Market Valuation 03:32 Why Did Kaz Leave $300M on the Table to Join Opendoor 04:44 Why Does Kaz Believe OPEN Can Be a Good Business When the Market Doesn’t 06:34 How does Kaz Feel About OPEN Becoming a Meme Stock? 17:25 Kaz’s $0 Salary but $1BN Stock Based Compensation 23:41 Oracle and OpenAI Partnership: WTF …

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Heading into the offseason with Pato O’Ward, Scott Dixon, Kyle Kirkwood, Christian Lundgaard, Rinus VeeKay, Josef Newgarden, Callum Ilott and Nolan Siegel 43:13

7d ago43:13

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PIT PASS INDY – SEASON 5, EPISODE 64 – Heading into the offseason with Pato O’Ward, Scott Dixon, Kyle Kirkwood, Christian Lundgaard, Rinus VeeKay, Josef Newgarden, Callum Ilott and Nolan Siegel September 16, 2025 Show host Bruce Martin has plenty more to unpack in the latest Pit Pass Indy as IndyCar heads into the offseason with a flurry of big ann…

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2 Years After Early Retirement | MHFI 285 1:14:01

5h ago1:14:01

1:14:01

Doug chats with Jackie and Jacob, a couple who left their W2 jobs to pursue Financial Independence and extensive travel adventures. They discuss traveling in South America, living a minimalist lifestyle, navigating challenges of geo-arbitrage, and how they manage finances while optimizing for travel & embracing flexibility. They also share financia…

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Marketing Malpractice: Why AI Won’t Save You Without Strategy with David Poulos 33:46

1h ago33:46

33:46

Send us a text In this episode of the Human-First AI Marketing® podcast, Mike Montague sits down with veteran CMO David Poulos to diagnose one of the most common but costly mistakes in small business marketing today: relying on AI without a clear strategy. They unpack how AI often becomes a shortcut to mediocrity, amplifying generic content, skippi…

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Helen Castor on Richard II 27:37

9m ago27:37

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Today's great life is possibly more famous as a Shakespearean character - King Richard II who was deposed by his cousin Henry Bolingbroke in 1399. He's been chosen by historian Helen Castor, author of The Eagle and the Hart, who shines a light on what really happened towards the end of his reign. Also helping is Professor Emma Smith who explains wh…

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DeLorean & Chrysler Laser XE - Curt's 80s Digital Dash Story 37:15

9d ago37:15

37:15

Click here to share your favorite car, car story or any automotive trivia! Join hosts Christian and Doug as they dive into Curt Bellotti's incredible 1980s automotive journey featuring two iconic cars that defined an era. From his teenage years behind the wheel of a 1984 Chrysler Laser XE Turbo with its Knight Rider-inspired digital dash to finally…

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20VC: Mercor: From $1M to $500M in 17 Months: The Fastest Growing Company in the World | How to Think About Margins and Revenue Sustainability in AI | Why Evaluation Benchmarks in AI are BS Today with ... 1:01:16

9d ago1:01:16

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Brendan Foody is the Co-Founder and CEO @ Mercor, the fastest growing company in history. The company solves talent allocation in the AI economy and they have scaled from $1M to $500M in revenue in just 17 months. With a rumoured new funding round pricing the company at a whopping $10BN, the company has the likes of Benchmark, Felicis, Emergence, a…

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Episode 198: "On the Town with Suz and Doug" Review Taco Tuesday at Fuzzy's Taco Shop 4:34

2d ago4:34

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"On the Town with Suz and Doug" Review Taco Tuesday at Fuzzy's Taco Shop in Sarasota, FL.Note: We are not comped for our meals. (dougmilesmedia)

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20VC: Why AI SDRs are BS and Do Not Work | How to Use AI in Your Sales Team and Process to Win Today | What Skills Do All New Reps Need to Have in an AI First World with Amit Bendov, CEO @ Gong 1:06:20

12d ago1:06:20

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Amit Bendov is Co-Founder & CEO of Gong, the leading AI-sales platform. The company has raised over $600 million from some of the best in the world including Sequoia, Thrive, Salesforce and more. Gong has surpassed $300M in ARR, serves thousands of customers (including multiple Fortune 10s), and is valued at over $7BN. AGENDA: 00:00 – Why CRM Was A…

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#270: Bon Voyage? Changing Churches, Pastoral Responsibility, and Defending Firm Conviction 43:12

5d ago43:12

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Matt, Jady, and Nick discuss whether or not pastors should "happily release" people to other churches, good and bad reasons to leave a parish, and defending strongly held pastoral and denominational convictions.By Stand Firm

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AI for Sales: Automate the Work, Keep the Connection with Chad Burmeister 30:15

43m ago30:15

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Send us a text In this episode of the Human-First AI Marketing Podcast, host Mike Montague sits down with ⁨@thechadburmeister⁩ , host of the AI for Sales Podcast and veteran AI entrepreneur, to explore how small and mid-sized businesses can harness AI without losing the human touch. Chad shares practical, battle-tested strategies for building custo…

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20VC: Musk's $TRN Pay Package Broken Down | Ramp Hits $1BN ARR and Brex Hits $700M: Who Wins | OpenAI's $10BN Secondary Sale | Atlassian Buys The Browser Company for $610M | ASML Lead Roun into Mistral ... 1:27:56

13d ago1:27:56

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AGENDA: [00:05] Musk’s $1 Trillion Pay Package: The Breakdown? [00:15] Scale, Windsurf: Are Founders Just Mercenaries Chasing Cash Today? [00:21] Ramp at $1B ARR, Brex at $700M — Is AI Causing All Boats To Rise? [00:26] Sierra at $100M ARR Worth $10B — Bubble or Brilliant Bet? [00:30] Kleiner Perkins Invests $100M into Anthropic at $183BN… WTF? [00…

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Unpacking the end of the 2025 INDYCAR Series Season with Scott Dixon, Scott McLaughlin, Marcus Ericsson and much more 45:36

13d ago45:36

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PIT PASS INDY – SEASON 5, EPISODE 63 – Unpacking the end of the 2025 INDYCAR Series Season with Scott Dixon, Scott McLaughlin, Marcus Ericsson and much more September 9, 2025 Show host Bruce Martin has plenty to unpack in the latest Pit Pass Indy as IndyCar heads into the offseason with a flurry of big announcements. In addition to catching up on a…

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Retire Often: Mastering the Art of Mini Retirements – Jillian Johnsrud | MHFI 284 53:19

28m ago53:19

53:19

Doug chats with Jillian Johnsrud about all-things mini retirement including preparation, challenges, and key insights. They explore how to test what retiring might look like through sabbaticals and mini retirements, touch on the importance of adapting to a new lifestyle, and address common issues that arise, such as maintaining productivity and man…

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How I Got My Dad To Love The VW Beetle: Dave’s Air-Cooled Journey 48:41

15d ago48:41

48:41

Click here to share your favorite car, car story or any automotive trivia! Dave Abelow's love affair with Volkswagen Beetles began in middle school when a friend's family rolled into Connecticut from California in a stunning black oval-window Bug with red interior. What started as teenage infatuation evolved into a seven-Beetle odyssey spanning fiv…

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AI Sales Roleplays with Michael Ocean 32:07

4d ago32:07

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Send us a text Most salespeople dread roleplay training. It’s awkward, unrealistic, and rarely reflects the real challenges they face with prospects. In this episode, Mike Montague sits down with Michael Ocean, founder of Sell Me This Pen AI, to talk about a better way. Instead of building AI to replace sales reps, Michael built an AI-powered coach…

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DJ Deb Grant on John Prine 26:51

7d ago26:51

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DJ Deb Grant picks US mailman turned country-folk singer John Prine, whose beautiful songs captured the world in which he lived. Bob Harris, who first met him on the Old Grey Whistle Test, adds to the conversation. "I came to know him through him speaking about his own music - it's his character, his personality and his attitude that I fell for," s…

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20VC: ElevenLabs Hits $200M ARR: The Untold Story of Europe's Fastest Growing AI Startup | The Real Cost of AI from Talent to Data Centres | How US VCs are in a Different League to Europeans | The Future ... 1:14:06

16d ago1:14:06

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Mati Staniszewski is the Co-Founder and CEO of ElevenLabs, the world’s leading AI voice platform. Since launching in 2022, ElevenLabs has raised over $350M, most recently at a $3.3BN valuation, making it one of Europe’s fastest AI unicorns. The company counts Andreessen Horowitz, Nat Friedman, Daniel Gross, and Sequoia Capital among its backers. To…

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Episode 197: "On the Town with Suz and Doug" Review Patrick's Restaurant in Sarasota, FL 5:36

2d ago5:36

5:36

"On the Town with Suz and Doug" Review Patrick's Restaurant in Sarasota, FL. Note: We are not comped for our meals. (dougmilesmedia)

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20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader ... 1:10:09

18d ago1:10:09

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Alex Schultz is the Chief Marketing Officer and VP of Analytics at Meta, where he has spent nearly two decades shaping the company’s growth and marketing strategy. He has been instrumental in scaling Facebook, Instagram, and WhatsApp to billions of users worldwide. Alex is is also the author of Click Here: The New Rules of Marketing, the definitive…

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Sage Marketing Advice with James Hipkin 35:48

5d ago35:48

35:48

Send us a text Too many SMBs think a new headline, a prettier design, or the latest AI tool will magically turn their website into a lead machine. In this episode, Mike Montague sits down with marketing veteran James Hipkin to explain why most underperforming websites don’t have a copy or design problem; they have a strategy problem. You’ll learn w…

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#269: Practicing the (Wrong?) Way: John Mark Comer, Apprenticeship, and Becoming Like Christ 53:06

19d ago53:06

53:06

Matt, Jady, and Nick discuss John Mark Comer, his popular book, and his new/old definition of following Jesus...with a long (and vigorous!) digression about kenosis.By Stand Firm

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20VC: Anthropic Raises $13BN | Why Canva Will Not Direct List | OpenAI Buys Statsig for $1.1BN All Stock | Lovable Raising at $4BN + Vercel at $9BN: Justified or Not | Quarterly Results from SNOW, Mongo ... 1:14:22

20d ago1:14:22

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Agenda: 04:00 – Anthropic Raises $13BN: The Analysis? 19:00 – Is Zuck’s $14BN Scale bet the biggest blunder in AI? 27:00 – Lovable Raising at $4BN and Vercel at $9BN: Justified or Madness? 36:00 – Quarterly Results for Snowflake, Mongo, Okta, Zoom Skyrocket: Is B2B SaaS back from the dead? 48:00 – Is Jensen Huang right there will be $4TRN in AI gai…

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Team Penske’s Josef Newgarden Wins Season Finale in Nashville. Also, Team Penske and Will Power part ways after 17 seasons 48:02

21d ago48:02

48:02

PIT PASS INDY PRESENTED BY PENSKE TRUCK RENTAL – SEASON 5, EPISODE 62 – Team Penske’s Josef Newgarden Wins Season Finale in Nashville. Also, Team Penske and Will Power part ways after 17 seasons September 2, 2025 Show host Bruce Martin has plenty to unpack in the latest Pit Pass Indy Presented by Penske Truck Rental after the final race of the 2025…

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Mr. Money Mustache Defines Cheap vs. Frugal (Live CampFI) | MHFI 283 57:46

14d ago57:46

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Doug chats with a variety of guests at CampFI Rocky Mountain Week 1.5 including Pete Adeney (Mr. Money Mustache), Kristen Knapp (FI Friends Travel), and camp attendees Amanda, Tyler, & Roxanne. Pete & Kristen delve into the distinction between being cheap and frugal, sharing personal anecdotes and philosophies. The conversation shifts into other to…

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Ford 1000 Tractor to 1984 Mercedes 240D First Car - Croom’s Journey from Farm Life to Healthcare AI & Million-Mile Philosophy 39:50

22d ago39:50

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Click here to share your favorite car, car story or any automotive trivia! Croom Lawrence's automotive journey began at age 10 driving a Ford 1000 tractor on his Virginia farm, but his first real car defined an era - a 1984 Mercedes-Benz 240D diesel nicknamed the "Lime Limo." With 250,000 miles when he got it (and built to go a million), this legen…

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Boring Marketing Is Your Biggest Competitor in the AI Era with Jay Schwedelson 25:56

10d ago25:56

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Send us a text If your marketing blends in, it’s already losing. In this episode, Mike Montague sits down with @schwedelson , CEO of Outcome Media, founder of SubjectLine.com, and host of the Do This, Not That podcast, to talk about why “boring” is the silent killer of your campaigns. Jay shares why AI isn’t the enemy, but a partner for amplifying …

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Going the Extra Mile for Homeless Youth and Young Adults (ft. Quana Smith & Danielle Stephen, Coalition for the Homeless) 46:25

8d ago46:25

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Neither foster care nor homelessness are isolated issues. They both intersect with numerous social issues—including each other. For example, homelessness is a contributing factor to why many children end up in the child welfare system, and it’s also a risk factor that can impact youth who are already involved in or aging out of foster care. Of the …

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20VC: Cohere Founder on How Cohere Compete with OpenAI and Anthropic $BNs | Why Counties Should Fund Their Own Models & the Need for Model Sovereignty | How Sam Altman Has Done a Disservice to AI with ... 1:07:50

23d ago1:07:50

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Nick Frosst is a Canadian AI researcher and entrepreneur, best known as co-founder of Cohere, the enterprise-focused LLM. Cohere has raised over $900 million, most recently a $500 million round, bringing its valuation to $6.8 billion. Under his leadership, Cohere hit $100M in ARR. Prior to founding Cohere, Nick was a researcher at Google Brain and …

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Episode 196: "On the Town with Suz and Doug" Review Saturday Night Dinner at Gecko's In Sarasota Florida 5:34

9d ago5:34

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"On the Town with Suz and Doug" Review Saturday Night Dinner at Gecko's In Sarasota Florida. Note: We are not comped for our meals. (dougmilesmedia)

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Mr. Money Mustache: Tesla, Health at 50, Passions & Projects [bonus] MHFI 282.5 54:10

10d ago54:10

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Mr. Money Mustache joins me to answer YOUR questions. It’s part 2 so if you missed part 1, check it out from July 18, 2025. If you dig the show, see ways to support mile high FI since we’re ad-free. Questions… [time stamps below] What have you changed your mind on? Is Pete still Snowbirding to Arizona in the winters down to cul-de-sac? And was that…

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20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat ... 53:48

26d ago53:48

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Jason James is the Co-Founder of Tezi and one of the leading product minds in the valley. Prior to Tezi, Jason was the VP Product at Instacart and before that was Head of Product and Design at Thumbtack. AGENDA: 00:00 Product lessons scaling Instacart to $40B – what really moves the needle 02:15 Why “quick optimizations” won’t build billion-dollar …

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#268: Too Far East of Eden: Why We're Not Orthodox 46:14

12d ago46:14

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Matt, Jady, and Nick talk about Eastern Orthodoxy. They discuss the East's view of Scripture and tradition, theosis, the use of icons, models of the atonement, and the failure of Orthodox/Protestant dialogue.By Stand Firm

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Custom Apps & Data Science: Hunter Jensen on Winning the Last Mile 31:19

23d ago31:19

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Send us a text In this episode of the Human-First AI Marketing Podcast, host Mike Monague sits down with Hunter Jensen, founder and CEO of Barefoot Solutions, to explore how AI is transforming software development, data workflows, and productivity across industries. From building custom applications to launching Compass, an AI-powered, self-hosted …

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20VC: Anthropic's $10BN Round | Klarna's IPO Broken Down | Inside a16z's 72 Deal Seed Investment Machine | Martin Casado: Is Consensus Investing the Only Game | Why Satya is Chatting S*** on SaaS Apps ... 1:11:40

27d ago1:11:40

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AGENDA: 00:00 – Marc Benioff vs Snowflake, Databricks & Palantir: Who Wins the Data Cloud War? 05:10 – Does Benioff Feel The Need to Buy AI Talent Like Zuck Is? 09:00 – What Salesforce has Learned From Palantir on Forward Deployed Engineers? 18:00 – Will SaaS apps disappear in an AI world? Why Satya is Chatting S*** 23:40 – Are SDRs really screwe…

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Christian Rasmussen’s thrilling win at The Milwaukee Mile. Plus, Tony George, Alex Palou, Will Power, David Malukas, Conor Daly, Jacob Abel and Tim Broyles 58:20

28d ago58:20

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PIT PASS INDY PRESENTED BY PENSKE TRUCK RENTAL – SEASON 5, EPISODE 61 – Christian Rasmussen’s thrilling win at The Milwaukee Mile. Plus, Tony George, Alex Palou, Will Power, David Malukas, Conor Daly, Jacob Abel and Tim Broyles August 26, 2025 Show host Bruce Martin has seemingly miles worth of content from the Snap-On Milwaukee Mile 250 at The Mil…

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Is $1.7M Enough To Retire? … It’s Not So Simple… [rebroadcast] | MHFI 282 47:53

26d ago47:53

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Doug and Carl chat with listener Steve to review his plans for early retirement. Steve discloses his financial background, asset allocation, and current expenses, including a net worth of about 1.7 million dollars. The group addresses retirement projections along with potential risks of retiring in a down market and the importance of having a conti…

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Honda Civic Dreams to Custom Paint Master: Top Coat Garage Owner's Car Journey, NSX Hunt & Paint Secrets 47:49

29d ago47:49

47:49

Click here to share your favorite car, car story or any automotive trivia! Join automotive enthusiasts Christian and Doug as they dive deep into the car culture journey of Matt from Top Coat Garage. From his first Honda Civic hatchback inspired by Gran Turismo's legendary Spoon Sports builds to running a high-end custom paint and restoration shop, …

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AI Podcasting: How to Turn Conversations Into Clients with Doug Sandler 28:03

15d ago28:03

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Send us a text What if your next client wasn’t in your funnel, but sitting in your guest seat? In this episode, Mike Montague chats with podcasting strategist Doug Sandler of Turnkey Podcast about how small business owners can stop chasing downloads and start using their podcast as a smart, AI-assisted lead generation engine. Doug shares his proven…

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20VC: Do Margins Matter in AI? | Is Defensibility Gone For Good? | Is Vertical SaaS Dead in a World of AI | What SaaS Rules Are BS and No Longer Apply in a World of AI | The Future of Venture: Why Chanel ... 1:21:03

30d ago1:21:03

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Byron Deeter is a Partner at Bessemer Venture Partners, and one of the most renowned SaaS investors. Byron has led 19 unicorn investments, including IPO successes like ServiceTitan, Procore, Twilio, Box, Gainsight, Intercom, DocuSign, SendGrid. His portfolio includes eight companies that have gone public. Insane. Agenda: 00:00 – Why are the stakes …