Best Ryan McKinnon Podcasts (2024)

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EP 122: Okta CEO Todd McKinnon on Scaling to $13B, High-Stakes Decisions, and Market Dynamics 1:21:28

12m ago1:21:28

1:21:28

What does it take to scale a company from an idea to a $13B industry leader? In my latest episode, Okta CEO Todd McKinnon dives into the essential lessons he’s learned on high-stakes decision-making, managing up to the board, and competing against tech giants like Microsoft. Todd also reflects on his journey to founding Okta, his bold choice to tea…

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EP 121: Snowflake CEO Sridhar Ramaswamy on the Future of AI and Data 50:31

17h ago50:31

50:31

Nine months into his role as Snowflake’s CEO, Sridhar Ramaswamy sat down for a candid discussion on the journey so far & what’s ahead. He uncovered details about his transition to Snowflake CEO, the operational changes he’s put in place to accelerate product development, and his bold predictions for AI’s future—along with how he’s guiding a vision …

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EP 120: Evan Goldberg (Founder and EVP, Oracle NetSuite) on 26 Years of Operating Lessons Running NetSuite 1:17:14

14d ago1:17:14

1:17:14

Evan Goldberg has been leading NetSuite for 26 years and counting. In this episode, Evan reflects on the journey of building NetSuite—from launching it with Larry Ellison’s support, to scaling through its IPO, and eventually being acquired by Oracle for $9.3B. He shares his leadership philosophies around humor and empathy, lessons learned from Larr…

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EP 119: Drew Houston (CEO, Dropbox): Reflections on the 17+ Year Battle Against Big Tech 1:34:53

12d ago1:34:53

1:34:53

Drew Houston has now been CEO of Dropbox for over 17 years. In my latest conversation, he opens up about the pivotal leadership lessons he's learned, the mistakes that shaped the company, and the true challenges of going head-to-head with big tech. We also dive into the highs and lows of fundraising, how valuations can make or break a company traje…

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EP 118: Will Gaybrick (President of Product and Business, Stripe) on Capital Allocation, Org Design, AI, and Global Growth 1:42:18

2M ago1:42:18

1:42:18

Will Gaybrick joined Stripe as CFO after investing in the company at Thrive Capital. Over the past 9 years, now as President, he's helped grow Stripe's into one of the world's largest private startups. In this episode, we explore his impressive career journey—from Harvard Math to software engineering, Yale Law, venture capital, and now his leadersh…

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EP 117: Parker Conrad (CEO, Rippling) His Opinion on Founder Mode, Fundraising, and VC Advice 1:42:29

2M ago1:42:29

1:42:29

Parker Conrad has spent the last 8 years building Rippling into a $13B company, marking his redemption after being ousted from Zenefits. In his second appearance on the podcast, Parker and I discussed Paul Graham's "founder mode" essay and how he operationalizes it at Rippling. He also reflected on the key lessons he's learned throughout his career…

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EP 116: John Fieldly (CEO, Celsius) How He Saved Celsius From Near Bankruptcy to a $10B Company 1:06:53

2M ago1:06:53

1:06:53

Many know Celsius as a top energy drink brand today, but few are aware of the tumultuous journey CEO John Fieldly took to get it here. In the episode, John shared how the company nearly went bankrupt multiple times, lost 50% of its revenue overnight and even got delisted from the NASDAQ. Despite these challenges, John stepped up to rebuild the bran…

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178: The Full Sundae 3:23:22

3M ago3:23:22

3:23:22

Early in the project, I promised that the final final episode of this project would be "doing right" by this movie and watching it all in one sitting, as intended. And I'm here to proudly announce: PROMISES MADE, PROMISES KEPT. Look, this episode is 3 and a half hours long. It was livestreamed on Twitch on August 22, 2024, with the full movie playi…

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EP 115: Josh Wolfe (Co-Founder, Lux Capital) On Uncovering Hidden Opportunities 1:54:27

2M ago1:54:27

1:54:27

Josh Wolfe, co-founder and managing partner at Lux Capital, is a master at quickly understanding complex, emerging technologies. In our conversation, Josh shared how he identifies the next big thing, his contrarian views on nuclear energy, biotech, and robotics, as well as his thoughts on the state of the venture capital market today. (00:00) Intro…

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177: THE FINAL MIN 13:15

3M ago13:15

13:15

Well folks, that's it. Looks like ol' Frankie is gonna ride off into the sunset, head held high. And so am I. Thank you so much for joining me on this ill-advised but ultimately enlightening and enriching experience. It was fun, but I am glad for it to be over. One final episode remains: the full real-time watch through. See you then!…

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176: Monday, August 19 - 2 MINUTES REMAIN 10:28

3M ago10:28

10:28

By Ryan Simmons

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175: Friday, August 16 - 3 MINUTES REMAIN 7:37

3M ago7:37

7:37

By Ryan Simmons

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EP 114: Emery Wells (CEO, Frame.io) on Selling to Adobe for $1.3B, Working with SNL and High Pain Tolerance 1:41:57

3M ago1:41:57

1:41:57

Emery Wells is the co-founder and CEO of Frame.io, which he sold to Adobe in 2021 for nearly $1.3 billion. In our conversation, Emery shares his journey from NYC bartender to startup founder, including his agency work with Saturday Night Live that highlighted the pain points that led to Frame.io. We dive deep into his rejection of the lean startup …

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174: Thursday, August 15 - 4 MINUTES REMAIN 7:20

3M ago7:20

7:20

By Ryan Simmons

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173: Wednesday, August 14 - 5 MINUTES REMAIN 10:14

3M ago10:14

10:14

By Ryan Simmons

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172: Tuesday, August 13 - 6 MINUTES REMAIN 9:34

3M ago9:34

9:34

By Ryan Simmons

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171: Monday, August 12 - 7 MINUTES REMAIN 13:24

3M ago13:24

13:24

By Ryan Simmons

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170: Friday, August 9 - 8 MINUTES REMAIN 9:12

3M ago9:12

9:12

By Ryan Simmons

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EP 113: Dara Khosrowshahi (CEO, Uber) Lays Out the Path to Autonomous Vehicles 1:09:15

3M ago1:09:15

1:09:15

Dara Khosrowshahi runs one of the most complicated businesses in the world, Uber. Since taking over in 2017 Dara has led the company to profitability against all odds. In this episode, we touch on a number of things including Uber’s position on the future of Autonomous Vehicles (AVs), the challenges that were overcome in making Uber profitable, and…

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169: Thursday, August 8 - 9 MINUTES REMAIN 8:10

3M ago8:10

8:10

By Ryan Simmons

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168: Wednesday, August 7 - 10 MINUTES REMAIN 11:05

3M ago11:05

11:05

By Ryan Simmons

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167: Tuesday, August 6 - 11 MINUTES REMAIN 14:35

3M ago14:35

14:35

By Ryan Simmons

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166: Monday, August 5 - 12 MINUTES REMAIN 16:03

3M ago16:03

16:03

We're getting down to the wire. Also, Lilith joins this week!By Ryan Simmons

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165: Friday August 2 (3:06) 5:55

3M ago5:55

5:55

Finally bringing it full circle to the old folks' home, and a brutal exchange in a bank. It's that and more, on... The Irishmin!!!By Ryan Simmons

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EP 112: Mike Maples (Founding Partner, Floodgate): What Makes Startups Win & The Future of Venture Capital 2:03:48

3M ago2:03:48

2:03:48

Mike Maples is an 8x Midas List investor and founding partner at Floodgate Fund. In our conversation, we dive into his latest book, "Pattern Breakers: Why Some Startups Change The Future." Mike shares his frameworks on how top startups beat incumbents by redefining categories, and he reflects on his worst and best decisions. We also discuss what th…

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164: Thursday August 1 (3:05) 4:52

3M ago4:52

4:52

Help, Frank Sheeran (The Irishman) has fallen and he can't get upBy Ryan Simmons

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164: Wednesday July 31 (3:04) 6:04

3M ago6:04

6:04

It all starts with the pill organizers, and then it's all downhill from thereBy Ryan Simmons

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163: Tuesday July 30 (3:03) 6:40

3M ago6:40

6:40

The Final Mins continue as we start to get to the reeeeal good old man stuffBy Ryan Simmons

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162: Monday, July 29 (3:02) 10:02

3M ago10:02

10:02

We are officially in The Final Mins, folks. Only 17 more mins remain, including this one in this very episode. It's almost too hard to think about this all coming to an end, but end it must. I hope you'll join me for the last little push of this stupid little project.By Ryan Simmons

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161: Friday, July 27 (3:01) w/ Jesse 14:28

4M ago14:28

14:28

Man these guys are fuggin OLLLLLLDD!By Ryan Simmons

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EP 111: How Josh Reeves (CEO, Gusto) Built a $10B Company Serving Small Businesses 1:34:05

3M ago1:34:05

1:34:05

Josh Reeves has built Gusto into a nearly $10B company with over $500M in ARR, serving small businesses. In our conversation, Josh delves into Gusto’s 13-year journey, sharing insights on how they achieved product-market fit by initially targeting a very narrow niche. He also highlights the tactics they’ve used to build an intentional culture of hu…

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160: Thursday, July 25 (3:00) w/ Jesse 12:06

4M ago12:06

12:06

That's three hours!!!By Ryan Simmons

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159: Wednesday, July 24 (2:59) w/ Jesse 13:36

4M ago13:36

13:36

Wow we're almost at three hours in.By Ryan Simmons

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158: Tuesday July 23 (2:58) w/ Jesse 10:12

4M ago10:12

10:12

Free Zoom calls are limited in time. We found this out while recording.By Ryan Simmons

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157: Monday July 22 (2:57) with Jesse Cramer 15:21

4M ago15:21

15:21

#1 Min-head, friend of the show and former guest Jesse Cramer stops by again to help us close the gap of these final few weeks of mins!By Ryan Simmons

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156: Friday, July 19 (2:56) 8:48

4M ago8:48

8:48

Ooooooop!!!!By Ryan Simmons

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155: Thursday, July 18 (2:55) 5:19

4M ago5:19

5:19

oop!!By Ryan Simmons

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154: Wednesday, July 17 (2:54) 6:01

4M ago6:01

6:01

OofBy Ryan Simmons

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153: Tuesday, July 16 (2:53) 7:58

4M ago7:58

7:58

OooooooooffffBy Ryan Simmons

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152: Monday, July 15 (2:52) 12:22

4M ago12:22

12:22

OooooooooooooofffBy Ryan Simmons

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151: Friday, July 12 (2:51) 6:33

4M ago6:33

6:33

"I'll call today!" "You'll call now." "I'll call now."By Ryan Simmons

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EP 110: How Eric Glyman (CEO, Ramp) Runs One of The Fastest Growing Startups 1:33:52

4M ago1:33:52

1:33:52

Eric Glyman (CEO, Ramp) shared his operating playbook for leading one of the fastest-growing startups on his second appearance on the podcast. We also explored the unique ways Ramp leverages AI internally, strategies for startups to build moats in AI, and the concept of self-driving money. We concluded with one of the most profound and thoughtful d…