Best Ryan Dempsey Podcasts (2025)

1
Howie: The AI Secretary | Austin Petersmith, Co-founder and CEO 1:39:50

Play Pause

5h ago1:39:50

1:39:50

Austin Petersmith is the Co-founder and CEO of Howie, the AI secretary. We talk about why AI assistants are so hard to build, why they decided to build Howie super narrow, and everything that went into their brand, name, and viral launch. Thank you to Adam D’Augelli, Sophia Amoruso and Alex Cohen for help brainstorming topics for the conversation. …

1
Stop Coding Emails: Loops Co-founder and CEO Chris Frantz 1:16:44

7d ago1:16:44

1:16:44

Chris Frantz is the Co-founder and CEO of Loops, the email platform for software companies. We get into why sending emails is still a big problem, his hilariously simple framework for building products, getting in to YC with a last minute application, and why they skipped raising a Series A. We also talk through Chris decade of working in marketing…

1
Untold Startup Lessons from Dozens of Academic Research Papers with Dan Gray at Equidam 2:06:15

14d ago2:06:15

2:06:15

Dan Gray is the Head of Insights at Equidam. If you’re a tech and investing nerd like us, you’ll love this conversation. We cover everything Dan’s learned reading dozens of academic research papers on startups and venture capital, debunking many popular narratives of the industry. We talk about the dangers of pre-mature startup scaling, the importa…

1
Rethinking Asset Allocation, The Past Present and Future of Venture Capital | Dan Feder, University of Michigan 1:52:28

23d ago1:52:28

1:52:28

Dan Feder is a Senior Managing Director of Investments at the University of Michigan’s $18 billion endowment. Our two hour conversation talks through the past, present, and future of all things venture capital, and investing more broadly. Dan lays out the case for why most institutional investors should change how they approach asset allocation, wh…

1
Inside Intercom’s AI Turnaround, Why Software Companies Must Train Their Own Models | Eoghan McCabe, Co-founder and CEO 1:59:06

29d ago1:59:06

1:59:06

Eoghan McCabe is the Co-founder and CEO of Intercom, building Fin.ai, the AI customer service company. This was an extremely candid, two hour conversation going inside every detail of how Intercom was the first late stage software company to successfully re-architect itself to be AI-native. Intercom just announced they’ve built their own customer s…

1
How To Generate Alpha in Venture Capital | Albert Azout, Level Ventures 1:20:56

1M ago1:20:56

1:20:56

Albert Azout is the Co-founder and Managing Partner of Level Ventures, combining first-principles thinking with state-of-the-art data science to back and build top seed-stage firms and their breakout companies. Venture investing is hard, and this conversation covers all their research unpacking exactly how to generate alpha. We also talk about how …

1
The Ocean: Earth’s $2.5 Trillion Last Frontier | Will O’Brien, Co-founder of Ulysses 1:50:43

1M ago1:50:43

1:50:43

Will O’Brien is the Co-founder of Ulysses, building autonomous, low cost robots for the ocean. Will considers the ocean humanity’s next great frontier. It makes up over $2.5 trillion of economic activity, considering things like fishing, aquaculture, shipping, mining, communications infrastructure, and defense. Yet we know more about the surface of…

1
How to Build a Content Strategy + CPG Brand Lessons | Isaac Medeiros (Mini Katana, Kanpai Foods) 1:15:22

2M ago1:15:22

1:15:22

Isaac Medeiros is the Founder of Mini Katana and Kanpai Foods. Isaac’s content gets over 1 billion views per month. Our conversation gets into content strategy from a high level down to tactical decisions, differences between the TikTok and YouTube algorithms, and how AI will impact content creation. We also get into Isaac’s origin story building c…

1
The Past, Present, and Future of AI, Robotics, Venture Capital, Crypto | Why Deep Tech Startups Mess up Value Capture | Michael Dempsey, Managing Partner, Compound 1:58:21

2M ago1:58:21

1:58:21

Michael Dempsey is the Managing Partner at Compound, a thesis-driven, research-centric investment firm. We spent two hours talking through the past, present, and future of a bunch of topics in technology and investing. Michael started investing in AI in 2016. He was the first investor in now-unicorns Runway and Wayve. But he hasn’t done much AI inv…

1
Ryan Hoover on Growth Flywheels, Building Communities, Helping Founders, LP Investing 1:38:21

2M ago1:38:21

1:38:21

Subscribe to my newsletter to get every episode + the transcript in your inbox every week. Ryan Hoover is the Founder of Product Hunt and Weekend Fund. Ryan’s probably helped more founders launch their products than anyone else on Earth. We talk about starting Product Hunt as an email list, and he open sources the growth flywheel that propelled it …

1
PhD to $100M Revenue: Rebuilding SMB Lending with AI | Sahill Poddar, Co-founder and CEO of Parafin 1:25:17

2M ago1:25:17

1:25:17

Sahill Poddar is the Co-founder and CEO of Parafin, helping marketplaces, vertical SaaS, and point of sale providers offer financial services their merchants. Sahill and his team have quietly built Parafin to nearly a $100m GAAP revenue run rate in only four years, and they've done it in an industry that's become a Silicon Valley graveyard: SMB len…

1
Sleeping in Parking Lots to $250M+ Revenue: How Handshake Built Gen Z's Career Platform, Inside its Fast Growing AI Data Labeling Business, Scaling a Three-Sided Marketplace, How AI Changes Hiring 1:36:34

3M ago1:36:34

1:36:34

Garrett Lord is the Co-founder and CEO of Handshake, the career and social network for Gen Z, connecting a million employers, 1,600 universities, and 18 million students and alumni. We talk through the explosive growth in Handshake’s human AI data labeling business, how AI is changing the job market and careers, advice for scaling a three-sided mar…

1
Solving the Hardest Problems in Dev Tools | Jake Cooper, Founder of Railway 1:28:04

3M ago1:28:04

1:28:04

Jake Cooper is the Founder of Railway. This conversation explores how AI accelerates the need for strong backend infrastructure, when to build vs buy in AI software, and why there are only two moats: solving hard problems and doing hard things. We also unpack Railway’s bold product bets, like enabling creators to earn revenue with backend templates…

1
How WordPress Powers 43% of the Internet | Matt Mullenweg, Co-founder and CEO, Automattic 1:28:56

3M ago1:28:56

1:28:56

Today’s guest is Matt Mullenweg, Co-founder of WordPress, which powers over 43% of all websites on the internet, and founder of Automattic. Our conversation explores the 2000’s internet, the early days of Automattic, and the decisions and philosophies that set them up for success 20 years later. We talk open source software, why Matt’s such a big p…

1
Gamma's Journey to $50M ARR with 30 Employees | Co-founder and CEO Grant Lee 1:31:08

3M ago1:31:08

1:31:08

Grant Lee is the Co-founder & CEO of Gamma, building instant PowerPoints, presentations, and websites with AI. As someone who’s made a lot of decks, its refreshing how Gamma thinks about slides starting with the words and narrative, using AI to build the design around the story. Gamma has put up impressive metrics, growing from zero to $50 million …

1
Inside the $2 Trillion Employee Benefits Market | Ryan Sachtjen, Threeflow 1:53:41

4M ago1:53:41

1:53:41

Ryan Sachtjen is the Co-founder and CEO of Threeflow, building software for employee benefits brokers and insurance carriers. We start with a deep dive into the nearly $2 trillion dollar employee benefits market, including the structural issues that actually give the smallest companies the most leverage. We also talk about insurance more broadly, A…

1
How to Raise a VC Fund Today, How AI is Changing Fintech, Traits of Top Emerging Managers, Why Everyone is Selling Secondaries, Triple-Layered SPVs | Samir Kaji, Co-founder and CEO of Allocate 1:42:03

4M ago1:42:03

1:42:03

Samir Kaji is the Co-founder and CEO of Allocate. This conversation is a deep dive into the private markets, the evolution of venture capital as an asset class, and how there are now 10x more private investment firms than public companies. We also unpack why 90% of venture funds simply can’t raise capital right now, advice for anyone raising a fund…

1
How to Skip Your Seed, Pre-Seed Lessons Building Afore to $500M+ AUM | Anamitra Banerji 1:35:56

4M ago1:35:56

1:35:56

Anamitra Banerji is the Co-founder of Afore Capital, an SF-based VC firm that specializes in investing in pre-seed stage companies. Our conversation gets into the evolution of Pre-Seed as a category, why Pre-Seed is more than option checks, what Afore looks for when backing founders before they even have a product, how to skip your Seed and go stra…

1
Benchmark’s Eric Vishria on Going Zero to $100M ARR in 12 Months, Archetypes of Top AI Founders, Why Storytelling is a Superpower, How Benchmark Makes New Investments 1:45:51

4M ago1:45:51

1:45:51

Eric Vishria is a General Partner at Benchmark Capital. Our conversation goes inside the new class of startups going zero to $100 million ARR in 12 months, the ways AI is changing company building, and how Eric and Benchmark make new investments. We get into the risk rewards of Series As today, how Benchmark competes to work with founders, and and …

1
Samsara’s Journey to $26B Public Company | Sanjit Biswas, Co-founder and CEO 1:32:03

4M ago1:32:03

1:32:03

Sanjit Biswas is the Co-founder and CEO of Samsara, the fleet management and safety platform. At the time of publication, Samsara is a public company worth over $26 billion, and we unpack how exactly they went from zero to run rating at over $1.5 billion in revenue in ten years. We get into using AI to impact the physical world, how Samsara uses AI…

1
Michael Kim @ Cendana | Lessons from the Top VCs, How Cendana Does Diligence, Portfolio Construction Best Practices, the 60x Rule, How Seed Funds Compete vs Multi-stage, Inside Cendana's Early Days 1:54:58

5M ago1:54:58

1:54:58

Michael Kim is the Founder of Cendana Capital, a fund of funds that makes anchor investments in very early stage VC funds. We talk characteristics of the best investors, how Cendana does diligence on fund managers, portfolio construction best practices, Michael’s “60x rule”, and why high ownership to fund size is the main driver of returns. We also…

1
How AI Changes Governments & Business Models, From $11 to $187M Exit | Mike Vichich, Pursuit 1:47:05

5M ago1:47:05

1:47:05

Mike Vichich is the Co-founder and CEO of Pursuit, which helps companies generate more revenue from the public sector. We talk about how AI is changing Helmer’s 7 Powers, how it’s impacting the government, if DOGE is actually working, building a startup in the Midwest, and how to disagree with your team. We also get into Mike’s prior company Wisely…

1
Unsullied by Sponsorship, Season 6 Finale 1:16:08

5M ago1:16:08

1:16:08

The Season 6 finale features a memorable appearance from the longtime, legendary Producer of Inside The NBA, Tim Kiely, as well as an array of call-ins to Chuck’s Answering Machine. Ernie and Charles hear from Biz Nasty & Frenchie, talk about playing pickup hoops with The Undertaker, answer the question “has Chuck ever blinked at a bar tab?”, and r…

1
Ultimate Startup Growth Playbook, Using AI to Automate Operations | Sam Ross, Numeral 2:01:12

5M ago2:01:12

2:01:12

Sam Ross is the Co-founder and CEO of Numeral. This conversation is a master class on all things growth at the zero to one stage. We talk early growth lessons from Airbnb, and stories from being one of the largest, earliest Facebook advertisers. We get into working backwards from pockets of strong demand to find business ideas, how to establish ear…

1
Scaling Amplitude to $300M ARR with Co-founder and CEO Spenser Skates 1:44:04

5M ago1:44:04

1:44:04

Spenser Skates is the Co-founder and CEO of Amplitude. Our conversation gets into the importance of data in product design and company building, how Amplitude is thinking about AI, and the future of user responsive software. We also get into the early days of building Amplitude, when to go multi-product, how to construct your board as a startup, hi…

1
Lessons Going Zero to $40M ARR in Two Years | Dan Lorenc, Chainguard 1:14:56

6M ago1:14:56

1:14:56

Dan Lorenc is the Co-founder and CEO of Chainguard, the safe source for open source. The internet runs on free, open source software. But as its risen in popularity, its become the latest attack point targeted by hackers and nation states. This conversation with Dan gets into the history of open source software, cloud computing, Linux, the software…

1
Hands of Time + Eric Church & Mike Sielski 1:16:10

6M ago1:16:10

1:16:10

Eric Church enters The Steam Room to indulge Chuck’s new interest in Country music, talk about his relationship with Michael Jordan, and explain why golf means so much to him. Mike Sielski joins to discuss his new book, “Magic in the Air”, share stories about the history of the slam dunk, and put the Chuckster on the spot about why he never partici…

1
Surviving Two Seed Extensions, Fixing Auth for AI Agents | Clerk Founder & CEO Colin Sidoti 1:39:38

6M ago1:39:38

1:39:38

Colin Sidoti is the Co-founder and CEO of Clerk, the best way to build authentication and user management. I loved this conversation, because Colin is currently in the arena building Clerk. It has not been easy, and he takes us inside some of the harder moments of the past six years. We hit on three main themes: authentication; lessons raising mult…

1
Building Verkada, the $4.5B Physical Security Company | Filip Kaliszan, Founder and CEO 1:42:51

6M ago1:42:51

1:42:51

Filip Kaliszan is the Founder & CEO of Verkada, the physical security company. Verkada started in 2016 by building the best camera for physical security teams, and has since evolved into a full suite of security products for buildings. Filip takes us inside Verkada’s rapid growth to almost a billion in annual revenue, over 2,000 employees, and rais…

1
Forage: The Trillion Dollar Opportunity in Restricted Payments | Ofek Lavian 1:13:06

6M ago1:13:06

1:13:06

Ofek Lavian is the Co-founder and CEO of Forage, the mission driven payments company. This is a special episode, because I’m an investor in Forage, and Ofek shares everything he’s learned building the company. We go deep on food stamps, also known as EBT or SNAP, the government program that provides over $200 billion dollars per year in benefits th…

1
e5. 108: Engineering Logic? 1:30:23

7M ago1:30:23

1:30:23

Jw David and Paul are joined again by david betteridge to dicsuss what makes logic in engineering?

1
How the World’s Most Active Angel Investor Operates | Ed Lando, Founder of Pareto Holdings 1:44:42

7M ago1:44:42

1:44:42

Ed Lando is the Co-founder of Pareto, where he’s been an early investor in over 25 unicorns, started and incubated over 10 companies, and was recently named the most active angel investor in the world according to Crunchbase. We get into how Ed first got started angel investing, how he built up deal flow, why he’s historically kept a low profile, a…

1
e5. 107: Design Debate 1:23:10

7M ago1:23:10

1:23:10

Paul sits confused while JW, the ninja and guest David Betteridge and Krish from India debate deisgn issues. a true Level 4 podcast

1
Alloy’s Unconventional Path to $1.5B with Tommy Nicholas, Co-founder and CEO 1:29:54

7M ago1:29:54

1:29:54

Tommy Nicholas is the Co-founder and CEO of Alloy, the identity and fraud prevention platform trusted by over 700 financial service companies. Our conversation explores the early days of fintech, why more consumer financial protections actually lead to more fraud, and gets into the weeds of various tactics he’s learned building a technical platform…

1
e5. 106: BS 4163 51:33

7M ago51:33

51:33

JW sparkninja and paul take a high level tour of BS 4163, essential if your a tutor.

1
War Damn Madness + Bruce Pearl 1:04:38

7M ago1:04:38

1:04:38

Bruce Pearl enters The Steam Room to somehow get Charles even more fired-up about Auburn heading into March Madness, and to discuss whether the SEC may be even tougher in basketball than football this year. Ernie and Chuck talk Timothée Chalamet, embarrassing moments, perfect days, and the worst time to raise ticket prices. Learn more about your ad…

1
The $750 Billion AI Opportunity in Customer Service | Mike Murchison, Co-founder and CEO of Ada 1:32:45

7M ago1:32:45

1:32:45

Mike Murchison is the Co-founder and CEO of Ada, the AI-powered customer service automation platform. Ada’s product and scale puts Mike at the forefront at how AI is changing software and labor markets, and this conversation felt like both a glimpse into the future, and a look into the past, at a story of pure grit and determination, working seven …

1
e5. 105: Modern Apprenticships discussion 1:27:21

7M ago1:27:21

1:27:21

The chaps discuss the modern apprentichsip and if it does and can serve well the trade.

1
Make It Matter + General Martin Dempsey 1:06:42

7M ago1:06:42

1:06:42

General Martin Dempsey enters The Steam Room for an enlightening conversation about leadership, his role as Chairman of USA Basketball, and embracing the concept of ‘creative friction’. Ernie and Charles give flowers to Diana Taurasi, discuss their favorite Oscar nominees, debate the duality of Kenny Smith, and the Chuckster tells a story about how…

1
Why Founders are Moving to Chattanooga, Tennessee to Lock-in | Cam Doody at Brickyard 1:45:47

8M ago1:45:47

1:45:47

Cam Doody is the Co-founder and General Partner of Brickyard, the venture capital firm moving founders to Chattanooga, Tennessee to lock-in with no distractions until they find product market fit. Brickyard is one of the most unique venture firms you’ll ever come across, and we get into how it how it was inspired by a 16x fund based in Chattanooga,…

1
e5. 104: Large Scale EV 1:13:06

8M ago1:13:06

1:13:06

The ninja drives us through a summary of large scale EV challenges

1
Stealing Money + Jason Kelce 1:05:58

8M ago1:05:58

1:05:58

Jason Kelce enters The Steam Room to toast the Eagles Super Bowl victory, defend the ‘tush push’ (even though “it sucks”), reflect on Travis’s upcoming decision about whether to retire or keep playing, and shed light on the impact Taylor Swift fans have had on the popularity of his ‘New Heights’ podcast. Ernie & Charles discuss what it’s really lik…

1
Zero to $20m ARR in Two Months: Inside Bolt’s 7-Year Journey to Overnight Success | Eric Simons, Co-founder & CEO 1:52:57

8M ago1:52:57

1:52:57

Eric Simons is the Co-founder and CEO of StackBlitz, best known for its breakout product Bolt, letting anyone build full stack apps from text, in the browser. Bolt launched in October of 2024, quickly growing from zero to a $20 million revenue run rate in two months, making it one of the fastest growing products ever. But Eric will be the first to …

1
Rick Zullo on Building Equal Ventures, Why Traction is Overrated, Advice for Emerging Managers 1:39:31

8M ago1:39:31

1:39:31

Rick Zullo is the Founder of Equal Ventures. Our conversation gets into Equal’s unique approach to venture capital, thinking more like public market and private equity investors, and why they also think traction is overrated at Seed. We talk through Equal’s thesis-driven model, employing a team of product owners, only investing in only 3 to 5 theme…

1
The Can-Do Mindset + Candace Parker 1:01:06

8M ago1:01:06

1:01:06

TNT Host, WNBA champion, & Tennessee basketball legend Candace Parker joins The Steam Room once again to talk about her memoir, which is set to release in June, the craziness that ensued from the NBA Trade Deadline, and the best teams and players in college basketball currently. Chuck & Ernie discuss Subway commercials, All-Star Game competitivenes…