Best The Modeling Insanity Podcast Podcasts (2025)

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460: You Only Need A Few Deals Per Year To Live Off Real Estate 43:47

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1d ago43:47

43:47

Most investors think they need dozens of deals to change their life — Greg Gaudet proves otherwise. In this episode, he breaks down how he built a Maui lifestyle off just a handful of deals per year, including the $5,500/month rental that became his foundation. You’ll hear how he went from struggling with addiction to owning 20 doors, what he learn…

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20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency ... 1:08:30

1d ago1:08:30

1:08:30

John McMahon is widely regarded as one of the greatest enterprise-software sales leaders of all time. He's the only person to have served as Chief Revenue Officer at five public software companies: PTC, GeoTel, Ariba, BladeLogic and BMC Software. He helped scale BladeLogic from a startup into a public company — ultimately leading to its ~$880M sale…

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20VC: Anthropic Raises $30BN from Microsoft and NVIDIA | NVIDIA Core Business Threatened by TPU | Sam Altman's "War Mode" Analysed | Sierra Hits $100M ARR: Justifies $10BN Price? | Lovable Hits $200M ARR ... 1:30:09

2d ago1:30:09

1:30:09

AGENDA: 04:06 Anthropic's $30BN Investment from Microsoft and NVIDIA 07:01 Google vs. OpenAI: Sam Altman's "War Mode" Memo 15:27 NVIDIA's Customer Concentration: Bull or Bear 22:12 Is "War Mode" BS: Does Hyper-Aggressive Ever Work? 36:12 Sierra Hits $100M ARR: Justify $10BN Price? 46:14 Implementation is the Biggest Barrier to Enterprise AI Growth …

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459: 19 Rentals In One Year—John's WILD Pivot Story 45:14

3d ago45:14

45:14

When you hear how John Figueiredo went from running a $100M cannabis company, IPO’ing alongside Jay-Z, and literally burying cash underground… to buying 19 rentals in his first year, you’ll understand why his pivot into real estate is one of the wildest stories we’ve ever covered. In this episode, John breaks down the markets he chose, the partners…

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Risky Business #816 -- Copilot Actions for Windows is extremely dicey 58:07

10h ago58:07

58:07

In this week’s show Patrick Gray and Adam Boileau discuss the week’s cybersecurity news, including: Salesforce partner Gainsight has customer data stolen Crowdstrike fires insider who gave hackers screenshots of internal systems Australian Parliament turns off wifi and bluetooth in fear of of visiting Chinese bigwigs Shai-Hulud npm/Github worm is b…

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458: The Key To Choosing The Right Exit Strategy 14:35

4d ago14:35

14:35

In today’s episode, Nathan Brooks breaks down the real reason so many investors leave money on the table: they’re choosing the wrong exit strategy. He walks through the simple, practical way to think about wholesaling, wholetailing, and flipping — and what actually matters when comparing deals, judging neighborhoods, reviewing finishes, and setting…

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457: Turning A Single Lead Into $2.6M In Deals 15:37

5d ago15:37

15:37

Real estate agent John Apple breaks down how one segmented neighborhood list and a simple email drip turned into two transactions totaling $2.6M in volume. In this episode, he shares exactly how he circle-prospects every listing, the nurture sequence that finally triggered a response, and why treating your listings as lead-generation assets can unl…

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20VC: Base44's Maor Shlomo on How Vibe Coding Will Kill SaaS and Salesforce | Why it is BS that Vibe Coding Platforms Do Not Have Defensibility and Bad Margins | Why He Worries About Google, Not Replit ... 1:11:43

5d ago1:11:43

1:11:43

Maor Shlomo is the Founder and CEO of Base44, the AI building platform that Maor built from idea to $80M acquisition by Wix, in just 8 months. Today the company serves millions of users and will hit $50M ARR by the end of the year. Before Base44, Maor was the Co-Founder and CTO of Explorium. AGENDA: 00:05 – 00:10: How Vibe Coding is Going to Kill S…

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456: 6 Ways To Improve Your Cold Calling Today 18:17

8d ago18:17

18:17

Cold calling expert John Wahib returns to break down the six improvements that instantly upgrade your calling results — from choosing the right lists to avoiding spam ratings, dialing smarter, using better filters, fixing name-pronunciation issues, and leveraging DealMachine’s new Radius tool to find untouched leads. David and Ryan unpack each tact…

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20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster ... 1:19:22

8d ago1:19:22

1:19:22

Max Altman is Co‑Founder & Managing Partner at Saga Ventures, a US$125 M early‑stage fund. Before Saga Max was an investor with Apollo Projects, Hydrazine Capital and Altman Capital (where he helped deploy over US$500 M) into breakout names such as Rippling and Reddit. AGENDA: 03:55 – Venture Capital Is FULL of Tourists With Single-Digit IQs 06:20 …

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Risky Biz Soap Box: Greynoise knows when bad bugs are coming 37:51

9d ago37:51

37:51

In this sponsored Soap Box edition of the podcast, Andrew Morris joins Patrick Gray to talk about how Greynoise can often get a 90 day heads up on serious vulnerabilities. Whether it’s malicious actors doing reconnaissance or the affected vendors trying to understand the scope of the problem, it seems that mass scanning activity lines up pretty nic…

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20VC: Cursor Raises $2.3BN: Who Wins the Coding War | Peter Thiel and Softbank Sell NVIDIA: Analysed | Why Venture Capital Will Hit $1TRN and the Opening of Retail | Why Stripe and the Best Companies Will ... 1:22:38

9d ago1:22:38

1:22:38

AGENDA: 04:47 Cursor Raises $2.3BN at $29BN Valuation 11:36 What Gemini 3 Means for Lovable, Cursor and Replit 30:54 Peter Thiel and Softbank Sell NVIDIA: The Bubble Bursting? 48:54 Oracle Credit Default Swaps: The Risk is Increasing 01:07:22 Stripe Does Tender at All-Time High: Why the Best Companies Will Never IPO 01:19:18 Why Retail WIll Cause a…

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455: $500K Wholesaling At 19 & 22 (Insane) 23:20

10d ago23:20

23:20

Tyler Williams and Joshua Dochee share how they generated over half a million dollars in their first year by leaning into novations instead of traditional wholesaling. They break down the exact pitch they use, how they move deals in the middle of nowhere, why Tyler’s first contract happened in a high-school bathroom, and how this strategy lets them…

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Risky Business #815 -- Anthropic's AI APT report is a big deal 51:24

6h ago51:24

51:24

In this week’s show Patrick Gray and Adam Boileau discuss the week’s cybersecurity news, including: Anthropic says a Chinese APT orchestrated attacks using its AI It’s a day ending in -y, so of course there are shamefully bad Fortinet exploits in the wild Turns out slashing CISA was a bad idea, now it’s time for a hiring spree Researchers brute for…

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454: $17K Per Deal, Two Deals a Month (The Playbook) 14:38

11d ago14:38

14:38

Robert has spent 20 years using a completely unconventional system: marketing to everyone, dropping 20,000 voicemails a day, and consistently landing $17k average deals. He breaks down how volume, fast screening, and four simple offers reliably turn 15 conversations a day into two deals a month. He also shares why this strategy stays effective even…

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Shorts vs Long Form: Which Actually Grows Your Business? 6:02

12d ago6:02

6:02

🎬 Ready to start your podcast? Steal my free script and title ideas below. https://mailchi.mp/podcastprinciples.com/script Do you need 10–20 minute videos—or will a 60-second YouTube Short do the job? In this episode, we cut through the noise. You’ll learn when short form is perfect for reach and discoverability (including how Shorts can rank on Go…

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Is Podcasting Still Worth It in 2025? 22:02

12d ago22:02

22:02

🎬 Ready to start your podcast? Steal my free script and title ideas below. https://mailchi.mp/podcastprinciples.com/script Is podcasting still worth it in 2025? ..or is there a smarter way to get the same upside? In this episode we get brutally honest about when you shouldn’t start a show, why compliance-heavy industries (hello, financial advisors)…

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453: How Many Cold Calls You Actually Need For A Deal 23:36

12d ago23:36

23:36

If you’ve ever wondered how many cold calls it actually take to land a deal, David and Ryan break down the real numbers with DealMachine member Karim Mahmoud—a cold-calling veteran who now leads a team of 50 callers. Karim lays out the exact call counts, lead ratios, best call times, dialer setups, and the DealMachine filters his team uses to consi…

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20VC: Andrew NG on The Biggest Bottlenecks in AI | How LLMs Can Be Used as a Geopolitical Weapon | Do Margins Matter in a World of AI? | Is Defensibility Dead in a World of AI? | Will AI Deliver Masa Son ... 1:02:53

12d ago1:02:53

1:02:53

Dr. Andrew Ng is a globally recognized leader in AI. He is Founder of DeepLearning.AI, Executive Chairman of LandingAI, General Partner at AI Fund, Chairman and Co-Founder of Coursera. As a pioneer in machine learning Andrew has authored or co-authored over 200 research papers in machine learning, robotics and related fields. In 2023, he was named …

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20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify ... 1:11:23

15d ago1:11:23

1:11:23

Carl Rivera is the Chief Design Officer at Shopify, where he previously led both Merchant Services and the Shop App as VP of Product. Before joining Shopify through its acquisition of Tictail, Carl was the co-founder and CEO of Tictail, the "Tumblr for e-commerce," where he built one of the most beloved design-forward commerce platforms of its era.…

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452: The Right Way To Raise Money For Your Deals 35:19

15d ago35:19

35:19

Raising money for real estate isn’t as simple as asking your friends to invest—there’s a right way to do it. In this conversation, David and Ryan sit down with Devin Robinson to break down how investors can legally and safely raise capital using micro-funds. Devin explains why most people approach private money the wrong way, how fund structures re…

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20VC: Sequoia's Leadership Transition | Michael Burry Shorts NVIDIA and Palantir | Gamma Raises $100M at $2BN | Has Defensibility Died in a World of AI | Datadog Surges as Duolingo Plummets: What is Happening ... 1:15:50

16d ago1:15:50

1:15:50

AGENDA: 04:22 Sequoia's Leadership Transition 09:46 Michael Burry's Big Short on Nvidia and Palantir 17:41 Gamma Raises $100M at a $2BN Valuation 32:34 Does Defensibility Exist Today When Copying is Easy 40:31 Should All Funds Be Way More Diversified 47:12 How to Run a Fundraising Process & What Not To Do 57:57 Datadog Surges 20% and Duolingo Crash…

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451: He Flips 60 Homes Per Year—Here's How 29:09

17d ago29:09

29:09

Jason Velie from Cape Fear Cash Offer is flipping 60 homes a year—and he doesn’t even step foot inside them anymore. In this episode, he breaks down how he scaled from a few small deals to a fully systemized operation that runs like clockwork. You’ll learn how he built his team, funds his flips, and keeps 60 projects moving without losing control. …

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Risky Business #814 -- It's a bad time to be a scam compound operator 1:03:19

13d ago1:03:19

1:03:19

In this week’s show Patrick Gray and Adam Boileau discuss the week’s cybersecurity news, including: The KK Park scam compound in Myanmar gets blasted with actual dynamite China sentences more scammers TO DEATH While Singapore is opting to lash them with the cane Chinese security firm KnownSec leaks a bunch of documents Necromancy continues on NSO G…

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450: How To Build A List That Actually Gets Deals 15:10

18d ago15:10

15:10

Matt Kamp breaks down the exact framework behind a top-performing list — one that helps you find real motivated sellers for both land and single-family deals. After running over a thousand off-market trainings, he’s sharing the filters, data points, and strategy that actually lead to closed deals. Watch as he builds a list live inside DealMachine a…

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How to Get Any YouTube Video or Podcast to Appear in Google Search 5:13

19d ago5:13

5:13

🎬 Ready to start your podcast? Steal my free script and title ideas below. https://mailchi.mp/podcastprinciples.com/script Want your videos to show up in Google? In this episode, I break down a simple, repeatable playbook to rank without getting lost in SEO theory. We run a “tactical test” you can do today: think like your prospect, search their re…

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449: Investing In Parking Lots?! Here's Why 36:55

19d ago36:55

36:55

Most investors chase houses, but Kevin Bupp shares why he’s buying parking lots and mobile home parks instead. These low-maintenance assets can quietly build serious cash flow without the headaches of traditional real estate—and Kevin breaks down exactly how he finds them, funds them, and profits from them. KEY TALKING POINTS: 0:00 - Intro 0:22 - K…

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20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons ... 1:25:43

19d ago1:25:43

1:25:43

Ev Randle is a General Partner @ Benchmark, one of the best funds in venture capital. In their latest fund, they have Mercor ($10BN valuation), Sierra ($10BN valuation), Firework ($4BN valuation), Legora ($2Bn valuation) and Langchain ($1.4Bn valuation). To put this in multiples on invested capital, that is a 60x, two 30x and two 20x. Before Benchm…

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20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets 1:09:13

22d ago1:09:13

1:09:13

Chad Peets is one of the greatest sales leaders and recruiters of the last 25 years. From 2018 to 2023, Chad was a Managing Director at Sutter Hill Ventures. Chad has worked with the world's best CEOs and CROs to build world-class go-to-market organizations. Chad is currently a member of the Board of Directors for Lacework and Luminary Cloud and on…

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448: How To Actually Start In Real Estate (For Beginners) 17:10

22d ago17:10

17:10

Everyone talks about wanting to invest in real estate — but this conversation is about the moment you finally do. Moose Math sits down with David and Chris to unpack the real fears, excuses, and mindset shifts that stop most beginners before they ever buy their first property. You’ll hear how David built his rental portfolio from the ground up, wha…

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20VC: Navan IPO: Winners, Losers and is a $4.5BN Exit Enough in VC Today | Harvey Raises $150M at $8BN Price | Why Google is a Buy and Amazon is a Sell | Meta Down 10%, Is Zuck Struggling? 1:16:23

23d ago1:16:23

1:16:23

AGENDA: 04:27 Navan's IPO: Winners, Losers and 20% Crater 12:55 Harvey Raises $150M at an $8BN Valuation 35:36 Was Sam Altman Wrong to Snap at Brad Gerstner 41:25 Why GOOG is a Buy and Amazon is a Short 47:43 Meta Down 10%, Buy or Sell? 51:12 If You Have Not Accelerated with AI, You Are Dead 01:05:20 Why Now is the Best Time for Series A and Worst …

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447: Investors Asked Our CEO Everything—Here’s What Happened 16:35

24d ago16:35

16:35

At a recent event, David sat behind a table that read “I’m the CEO of DealMachine — ask me anything.” Investors took him up on it, pressing him with tough questions about off-market data, filters, and more. In this episode, you’ll hear his unfiltered answers and what truly sets DealMachine apart. KEY TALKING POINTS: 0:00 - Intro 0:10 - How David Fi…

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Risky Business #813 -- FFmpeg has a point 1:05:08

24d ago1:05:08

1:05:08

In this week’s show Patrick Gray and Adam Boileau discuss the week’s cybersecurity news, including: We love some good vulnerability reporting drama, this time FFmpeg’s got beef with Google OpenAI announces its Aardvark bug-gobbling system Two US ransomware responders get arrested for… ransomware Memento (nee HackingTeam) CEO says: Sì, those are tot…

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446: How To Do Short Sale Deals (Overlooked Strategy) 14:52

25d ago14:52

14:52

Most investors walk away when a seller owes more than the house is worth. In this episode, Jiries Dawaher reveals how to turn those “dead” deals into real profits with short sales — an overlooked strategy that can help you close more off-market deals right now. He breaks down what short sales are, how to find these opportunities, and towards the en…

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How to Replace Your Marketing with a Podcast in 90 Days | Ryan Sullivan 40:48

26d ago40:48

40:48

🎬 Ready to start your podcast? Steal my free script and title ideas below. https://mailchi.mp/podcastprinciples.com/script I sat down with Jared Smith to show how a podcast can replace most of your marketing in ~90 days. Since 2020, my team at Podcast Principles has helped 2,000+ clients rack up 15M+ views and 500K downloads, and in this episode I …

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445: Make $1M From One Real Estate Deal By Splitting The Lot 10:34

26d ago10:34

10:34

New 2025 zoning rules are quietly changing the game for real estate investors. In this episode, David breaks down how ADUs and lot-splitting can unlock million-dollar deals—often in cities you’d never expect. He walks through exactly how to find these properties inside DealMachine, the filters to use, and the hidden data most investors miss. KEY TA…

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20VC: Cohere's Chief AI Officer on Why Scaling Laws Will Continue | Whether You Can Buy Success in AI with Talent Acquisitions | The Future of Synthetic Data & What It Means for Models | Why AI Coding ... 57:34

26d ago57:34

57:34

Joelle Pineau is the Chief AI Officer at Cohere, where she leads research on advancing large language models and practical AI systems. Before joining Cohere, she was VP of AI Research at Meta, where she founded and led Meta AI's Montreal lab. A professor at McGill University, Joelle is renowned for her pioneering work in reinforcement learning, rob…

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444: Top 10 Leadership Mistakes That Hold Real Estate Investors Back 20:20

29d ago20:20

20:20

Every investor wants more deals, but most don’t realize that leadership—not lead generation—can be the main problem that’s holding them back. In this episode, David shares the 10 biggest leadership mistakes that quietly sabotage real estate investors as they build teams. From poor hiring to weak accountability, you’ll learn how to avoid the traps t…

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20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable 1:31:49

29d ago1:31:49

1:31:49

🎧 20VC x Tim Ferriss — Full Episode Timeline 00:00 – "How Do You Stay True to Yourself When You Have to Perform for the World?" 06:00 – "Why Tim Ferriss Refused to Go All-In on YouTube" 09:00 – "You Don't Need 10 Million Fans—You Need 1,000 True Believers." 12:00 – "The Internet Is Not a Relevance Machine—It's a Sensationalism Machine." 15:00 – "Mo…

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20VC: a16z Raises $10BN in New Funds | Mercor Raises $350M at a $10BN Valuation | OpenAI Restructuring: Who Wins and Who Loses | Why IRR is a BS Metric and Three Ways to Win in VC Today 1:24:09

1M ago1:24:09

1:24:09

AGENDA: 05:17 OpenAI's Restructuring: Winners and Losers 17:17 Andreessen Horowitz's Raise $10BN in New Funds 26:38 Mercor Raises $350M at a $10BN Valuation 43:08 Spray and Pray: Does it Work: Data Breakdown 47:04 The Role of Option Checks Venture Capital 48:36 The Three Ways to Win in VC Today 54:26 Why IRR is a BS Metric and What Matters More 01:…

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443: How He Leveraged ADUs to Build $700K Equity in ONE DEAL 25:53

1M ago25:53

25:53

In this episode, David Lecko sits down with Edmond Bondoc to uncover how he built nearly $700,000 in equity on a single property by leveraging Seattle’s ADU laws. Edmond reveals the exact financing, design, and condo-ization strategy he used to add both an attached and detached ADU to one lot—turning a half-finished fixer into a wealth-building mac…

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Risky Business #812 -- Alleged Trenchant exploit mole is ex-ASD 1:06:14

1M ago1:06:14

1:06:14

In this week’s show Patrick Gray and Adam Boileau discuss the week’s cybersecurity news, including: L3Harris Trenchant boss accused of selling exploits to Russia once worked at the Australian Signals Directorate Microsoft WSUS bug being exploited in the wild Dan Kaminsky DNS cache poisoning comes back because of a bad PRNG SpaceX finally starts dis…

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442: The Case AGAINST Building a Huge Rental Portfolio 15:48

1M ago15:48

15:48

Think you need a massive portfolio to reach financial freedom? Think again. In this episode, Chad Carson breaks down why “going big” isn’t always the smartest move — and how a few great rentals can build serious wealth and give you your time back. You’ll learn his “small and mighty” approach to real estate, how just three rentals could snowball int…

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Your Podcast Strategy Is Costing You Views (Unless You Fix This) 48:48

1M ago48:48

48:48

🎬 Ready to start your podcast? Steal my free script and title ideas below. https://mailchi.mp/podcastprinciples.com/script Your podcast should grow your business, otherwise, what's the point? I sit down with my good friend Danny to unpack why a video-first podcast is the most versatile asset you can create. I detail how one 10+ minute recording int…

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441: How To Find Motivated Sellers (From A $100M Investor) 36:16

1M ago36:16

36:16

What if a $100M investor showed you exactly how he finds motivated sellers? In this exclusive DealMachine training, Thach Nguyen joins Matt Kamp to reveal the filters, data points, and exact formula he uses to build high-converting seller lists in any market. You’ll learn how to identify profitable neighborhoods, pick the right property types, and …

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20VC: Sequoia's David Cahn on The Winners and Losers in AI | The $0-$100M Revenue Club: Is Triple, Triple, Double, Double Dead? | The Future of Defence: Who Wins and Who Loses | How to Analyse Margins ... 1:14:23

1M ago1:14:23

1:14:23

David Cahn is a Partner at Sequoia Capital and one of the world's leading AI investors. At Sequoia David has led investments in Clay, Juicebox, Sesame, Kela, Stark, etc.. Before Sequoia, David was a General Partner @ Coatue where he led investments in Notion and Hugging Face. AGENDA: 00:00 We Are in an AI Bubble 05:04 Why Building Physical Data Cen…

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20Growth: How to Build a Paid Marketing Machine: ROAS (Return on Ad Spend) 101 | The Rise of User Generated Content and How to Use It | TikTok Ads: Expectations vs. Reality | Hiring for Growth: When and ... 1:16:18

1M ago1:16:18

1:16:18

Sandy Diao is one of the most exceptional growth leaders of the last decade. Sandy has scaled products to over 200M+ users and led growth teams at Descript, Meta and Pinterest. She is also a prolific writer all on things growth here. AGENDA: 03:59 Biggest Growth Lessons from Pinterest 08:01 What is a Good vs a Bad Growth Hypothesis 11:11 Common Mis…

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440: I Made $576k From One Cold Call—Here’s How 38:42

1M ago38:42

38:42

Ryan Haywood and his COO, Clint Keith, join David to share how one cold call led to a $576,000 wholesale deal from a single seller. They break down how they handled a 21-property portfolio, structured the contracts, verified a power of attorney, and found the right buyer to close it all in one shot. You’ll learn how to approach portfolio sellers, e…

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Episode 39 - Ignorance, Arrogance, or Stupidity...Or Maybe it's Just All Three with Special Guest Insider Tim Rhine 2:02:11

1M ago2:02:11

2:02:11

Send us a text Episode 39 - Ignorance, Arrogance, or Stupidity...Or Maybe it's Just all Three with Special Guest Insider Tim Rhine On this Episode, the Insanity Crew talk to Tim Rhine whose model was the one that was manhandled at the recent PatCon Show. This discussion adds more detail and insider information regarding the discussion from Episode …

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20VC: Why VC Today is Worse Than 2021 | Why Vertical SaaS is a Bad Investment Today | Why We Are Deluding Ourselves on Growth Expectations | Revolut Raises $3BN at a $75BN Valuation | Benchmark Adds Their ... 1:28:58

1M ago1:28:58

1:28:58

AGENDA: 04:50 Benchmark's New Partner: Everett Randall 10:19 Revolut Raises $3BN at a $75BN Valuation: Another Loss for Public Markets? 28:39 Why Today is as Bad as the Hype of COVID in 2021 32:10 Why Vertical SaaS is a Bad VC Investment Today 36:14 Why Everyone Investing in Legal SaaS Will Lose Money 44:16 Why King Making is More Real Than Ever 55…