Mike Maples, Jr.

Kara and Scott discuss California governor Gavin Newsom's veto of the AI bill that divided Big Tech, and Trump Media co-founders dumping $100 million worth of stock. Then, JD Vance and Tim Walz face off, Donald Trump's latest comments hit new lows, and is Kamala Harris leaning into crypto? Plus, a peek at OpenAI's financials reveals massive gains, but bigger losses. Will that be a problem for investors? Our Friend of Pivot is Mike Maples Jr., co-founder of the VC firm, Floodgate, and author of the new book, "Pattern Breakers: Why Some Start-Ups Change the Future." Mike talks about what makes for a successful start-up, and shares the story behind one of his biggest misses. Follow Mike at @m2jr Follow us on Instagram and Threads at @pivotpodcastofficial. Follow us on TikTok at @pivotpodcast. Send us your questions by calling us at 855-51-PIVOT, or at nymag.com/pivot. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Mike Maples, Jr.

Founding Partner

Floodgate

Silicon Valley investor Mike Maples Jr. is known for having a ‘Midas Touch.’ Think of a tech start-up that has changed your life in the last 20 years, and he was probably helping fuel its growth. Mike talks with host Reid Hoffman about the insights he’s gathered from decades of investing, which he shares in his new national bestseller book: Pattern Breakers. They also riff on how to build – and invest – in the AI revolution. Synthetic voiceover of Reid Hoffman used in this episode was produced by Respeecher with full consent and permission. Read a transcript of this episode: https://mastersofscale.com Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe You can find Pattern Breakers here: https://amzn.to/4d8fx9N See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Mike Maples, Jr.

Founding Partner

Floodgate

Mike Maples Jr. is a prolific angel investor and co-founder of early-stage venture firm Floodgate. Over the years, he’s taken a lot of bets. Some have paid off handsomely (Twitter, Twitch, Lyft and Bazaarvoice, for example). Others have not. On today's episode of Equity, Mary Ann sat down with Mike to dig into a number of topics, including some of his most memorable investments, the one that got away, what he looks for when evaluating startups that pitch him - and what Godzilla has to do with it. We also talked a bit about his new book that he co-authored with Peter Ziebelman called “Pattern Breakers. Why some startups change the future.” Press play and join the conversation! Equity is TechCrunch’s flagship podcast, produced by Theresa Loconsolo, and posts every Wednesday and Friday. Subscribe to us on Apple Podcasts, Overcast, Spotify and all the casts. You also can follow Equity on X and Threads, at @EquityPod. For the full episode transcript, for those who prefer reading over listening, check out our full archive of episodes over at Simplecast. Credits: Equity is produced by Theresa Loconsolo with editing by Kell. Bryce Durbin is our Illustrator. We'd also like to thank the audience development team and Henry Pickavet, who manages TechCrunch audio products. Learn more about your ad choices. Visit megaphone.fm/adchoices

Mike Maples, Jr.

Founding Partner

Floodgate

Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about: • The three elements of breakthrough startup ideas • Why you need to both think and act differently • How to avoid the “comparison trap” and “conformity trap” • The importance of movements, storytelling, and healthy disagreeableness in startup success • How to apply pattern-breaking principles within large companies • Mike’s one piece of advice for founders • Much more Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny. — Brought to you by: • Enterpret—Transform customer feedback into product growth • Anvil—The fastest way to build software for documents • Webflow—The web experience platform — Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr — Where to find Mike Maples, Jr.: • X: https://x.com/m2jr • LinkedIn: https://www.linkedin.com/in/maples/ • Substack: https://greatness.substack.com/ • Website: https://www.floodgate.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Mike’s background (03:10) The inspiration behind Pattern Breakers (08:09) Uncovering startup insights (11:37) A quick summary of Pattern Breakers (13:52) Coming up with an idea (15:30) Inflections (17:09) Examples of inflections (28:10) Insights (36:58) The power of surprises (47:36) Founder-future fit (55:33) Advice for aspiring founders (56:41) Living in the future: valid opinions (55:34) Case study: Maddie Hall and Living Carbon (58:40) Identifying lighthouse customers (01:00:53) The importance of desperation in customer needs (01:03:57) Creating movements and storytelling (01:24:22) The role of disagreeableness in startups (01:34:42) Applying these principles within a company (01:40:43) Lightning round — Referenced: • Pattern Breakers: Why Some Start-Ups Change the Future: https://www.amazon.com/Pattern-Breakers-Start-Ups-Change-Future/dp/1541704355 • Justin.tv: https://en.wikipedia.org/wiki/Justin.tv • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • The Unconventional Exit: How Justin Kan Sold His First Startup on eBay: https://medium.datadriveninvestor.com/the-unconventional-exit-how-justin-kan-sold-his-first-startup-on-ebay-4d705afe1354 • Kyle Vogt on LinkedIn: https://www.linkedin.com/in/kylevogt/ • The State of Telehealth Before and After the COVID-19 Pandemic: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9035352/ • The Craigslist Killers: https://www.gq.com/story/craigslist-killers • The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host): https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston • Michael Seibel on LinkedIn: https://www.linkedin.com/in/mwseibel/ • The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions ... and Created Plenty of Controversy: https://www.amazon.com/Airbnb-Story-Ordinary-Disrupted-Controversy/dp/0544952669 • Scott Cook: https://www.forbes.com/profile/scott-cook/ • Chegg: https://www.chegg.com/ • Aayush Phumbhra on LinkedIn: https://www.linkedin.com/in/aayush/ • Osman Rashid on LinkedIn: https://www.linkedin.com/in/osmanrashid/ • Okta: https://www.okta.com/ • The Man Who Makes the Future: Wired Icon Marc Andreessen: https://www.wired.com/2012/04/ff-andreessen/ • Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig/ • Qasar Younis on LinkedIn: https://www.linkedin.com/in/qasar/ • Paul Allen’s website: https://paulallen.com/ • Louis Pasteur quote: https://www.forbes.com/quotes/6145/ • What was Atrium and why did it fail? https://www.failory.com/cemetery/atrium • Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/ • Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/ • William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly • Maddie Hall on LinkedIn: https://www.linkedin.com/in/maddie-hall-76293135/ • Living Carbon: https://www.livingcarbon.com • Zenefits (now Trinet): https://connect.trinet.com/ • Sam Altman on X: https://x.com/sama • Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/ • Horsley Bridge Partners: https://www.horsleybridge.com/ • David Swensen: https://en.wikipedia.org/wiki/David_F._Swensen • Judith Elsea on LinkedIn: https://www.linkedin.com/in/judithelsea/ • 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319 • Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer • Lyft’s Focus on Community and the Story Behind the Pink Mustache: https://techcrunch.com/2012/09/17/lyfts-focus-on-community-and-the-story-behind-the-pink-mustache/ • Logan Green on LinkedIn: https://www.linkedin.com/in/logangreen/ • John Zimmer on LinkedIn: https://www.linkedin.com/in/johnzimmer11/ • Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks: https://www.lennysnewsletter.com/p/storytelling-with-nancy-duarte-how • Steve Jobs Introducing the iPhone at MacWorld 2007: https://www.youtube.com/watch?v=x7qPAY9JqE4 • Jonathan Livingston Seagull: https://www.amazon.com/Jonathan-Livingston-Seagull-Richard-Bach/dp/0743278909 • The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer • Robin Roberts on LinkedIn: https://www.linkedin.com/in/robin-roberts-393a934b/ • Skunkworks: https://www.lockheedmartin.com/en-us/who-we-are/business-areas/aeronautics/skunkworks.html • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery): https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson • Figma: https://www.figma.com/ • Atlassian: https://www.atlassian.com/ • Vinod Khosla: https://www.khoslaventures.com/team/vinod-khosla/ • Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing: https://www.amazon.com/Top-Five-Regrets-Dying-Transformed-ebook/dp/B07KNRLY1L • Chase, Chance, and Creativity: The Lucky Art of Novelty: https://www.amazon.com/Chase-Chance-Creativity-Lucky-Novelty/dp/0262511355 • Clay Christensen’s books: https://www.amazon.com/stores/Clayton-M.-Christensen/author/B000APPD3Y • Resonate: Present Visual Stories That Transform: https://www.amazon.com/Resonate-Present-Stories-Transform-Audiences/dp/0470632011 • Ferrari on Prime: https://www.amazon.com/Ferrari-Adam-Driver/dp/B0CNDBN672 • Montblanc fountain pens: https://www.montblanc.com/en-us — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Mike Maples, Jr.

Founding Partner

Floodgate

My guest today is Mike Maples, co-founder and partner of Floodgate. As a child of the computer revolution, Mike was deconstructing calculators in grade school, writing video games in high school, and inevitably found himself building businesses in Silicon Valley after college. After his success as an operator, Mike eventually transitioned to become a full-time venture investor in the 2000s, and has since built a track record that includes Twitter, Twitch, Lyft, Octa, and a long list of successful tech businesses.   I'm not sure I've recorded a conversation with more applicable ideas and advice for company builders. We discussed early insights and secrets, value hypothesis testing, customer development, growth, team orchestration, and a lot more.   This is a masterclass from somebody who has seen it all. Also, do not miss his answer to the kindest thing question at the end of the conversation. I hope you enjoy this great talk with Mike Maples.   For the full show notes, transcript, and links to mentioned content, check out the episode page here. -----   Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:03:08] - [First question] - His philosophy on the power of forcing a choice [00:04:43] - How he knows when he comes across a team that has an apple quality [00:07:39] - Exploring and hunting new inflections in ever-changing systems [00:10:37] - Why recognizing winning insights allows you to not have to predict the future [00:12:23] - Whether or not the evolving nature of the funding landscape changes his thinking [00:14:18] - An example of his insight framework and stress testing a team’s potential [00:17:21] - Practice reckless optimism [00:18:54] - Commonalities between teams and their ideas when they get inflections wrong  [00:20:12] - What the value hypothesis is and how to test it [00:22:15] - Ways that effective startup teams operate compared to big corporations  [00:25:36] - His involvement post-investment and where outsiders can be most helpful in a companies’ early days [00:28:34] - Lessons learned about finding, convincing, and marketing to their first customers  [00:32:13] - An example of early customer selection done phenomenally well [00:34:09] - Why it was possible for companies like Justin.TV and Lift to pivot so dramatically from their original ideas  [00:38:49] - Customer development and using good customers to your advantage [00:42:31] - Who went from founder to the best growth executive  [00:43:05] - What he thinks his firm will need to do to continue offering an apple to founders [00:46:08] - The most useful stress tests his firm can offer founders [00:46:52] - Defining category design and what the process of category design looks like [00:50:33] - Inflections he’s currently paying the most attention to [00:52:07] - His experience with an HP35 calculator and how it shaped his life  [00:54:41] - What venture capital may look like in the future [00:56:30] - The most difficult things he faces in his career [00:57:52] - Ways he’s learned to manage failure more effectively [00:59:06] - The kindest thing that anyone has ever done for him

Mike Maples, Jr.

Founding Partner

Floodgate

"If the customer doesn't scream, you don't have product-market fit." — Andy Rachleff Welcome to another episode of The Tim Ferriss Show. This time, we have a slightly different episode—a takeover by Mike Maples, Jr. Mike Maples, Jr. (@m2jr) and his firm, Floodgate, have invested in and supported many of the startups you might recognize — including Twitter, Twitch, Lyft, Chegg, and Okta, among others — long before they were household names. He's been on the Forbes Midas List eight times in the last decade, but he's much more than a successful investor. Mike has also succeeded as both a founder and operating executive. He's also simply a great guy and the first person who really taught me how to angel invest. For more on that background, listen to my interview with Mike at tim.blog/mikemaples. In this episode, however, Mike speaks with Andy Rachleff (@arachleff), co-founder of Wealthfront and Benchmark Capital, about two of the biggest questions that should be on every start-up founder's mind: How do you reach "product-market fit" (a term that Andy coined), and how do they know when you've achieved it? Andy has known many of the start-up world's giants and synthesized their lessons, so you will also hear what Andy learned from Don Valentine of Sequoia, Scott Cook of Intuit, Reed Hastings of Netflix, Geoffrey Moore, Clay Christensen, Eric Ries, and Steve Blank. The audio from this conversation is from the premiere episode of Mike's brand-new podcast, Starting Greatness, which I encourage you check out. There are some incredible guests coming. So, if you like this conversation between Mike and Andy, be sure to subscribe to Starting Greatness on Apple Podcasts, Spotify, Overcast, or wherever you get your podcasts. You can also check out the website at greatness.floodgate.com, and on Twitter you can follow Mike at @m2jr and Andy at @arachleff. Please enjoy! This podcast is brought to you by Peloton, which has become a staple of my daily routine. I picked up this bike after seeing the success of my friend Kevin Rose, and I’ve been enjoying it more than I ever imagined. Peloton is an indoor cycling bike that brings live studio classes right to your home. No worrying about fitting classes into your busy schedule or making it to a studio with a crazy commute. New classes are added every day, and this includes options led by elite NYC instructors in your own living room. You can even live stream studio classes taught by the world’s best instructors, or find your favorite class on demand. Peloton is offering listeners to this show a special offer: Enter the code you heard during the Peloton ad of this episode at checkout to receive $100 off accessories with your Peloton bike purchase. This is a great way to get in your workouts, or an incredible gift. That’s onepeloton.com and enter the code you heard during the Peloton ad of this episode to receive $100 off accessories with your Peloton bike purchase. This podcast is also brought to you by 99designs, the global creative platform that makes it easy for designers and clients to work together to create designs they love. Its creative process has become the go-to solution for businesses, agencies, and individuals, and I have used it for years to help with display advertising and illustrations and to rapid prototype the cover for The Tao of Seneca. Whether your business needs a logo, website design, business card, or anything you can imagine, check out 99designs. You can work with multiple designers at once to get a bunch of different ideas, or hire the perfect designer for your project based based on their style and industry specialization. It's simple to review concepts and leave feedback so you'll end up with a design that you're happy with. Click this link (99designs.com/tim) and get $20 off plus a $99 upgrade. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. For show notes and past guests, please visit tim.blog/podcast. Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Interested in sponsoring the podcast? Please fill out the form at tim.blog/sponsor. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss Instagram: instagram.com/timferriss Facebook: facebook.com/timferriss YouTube: youtube.com/timferriss Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Mike Maples, Jr.

Founding Partner

Floodgate

Mike Maples, Jr. (@m2jr) is the man who taught me how to invest. He's one of my favorite people and a personal mentor. He is a partner at Floodgate, a venture capital firm that specializes in micro-cap investments in startups. He has been on the Forbes Midas List since 2010 and named one of Fortune magazine's "8 Rising VC Stars." Before becoming a full-time investor, Mike was inolved as a founder and operating executive at back-to-back starup IPOs, including Tivoli Systems (acquired by IBM) and Motive (acquired by Alcatel-Lucent). Some of Mike's investments include Twitter, Twitch.tv. ngmoco, Weebly, Chegg, Bazaar-voice, Spiceworks, Okta, and Demandforce. Enjoy! This podcast is brought to you by ConvertKit. After trying the competition, this is the only email tool that has made email marketing intuitive for my team without sacrificing any of the features and benefits I need to run a profitable business. It's easy-to-use systems, split testing, resending technology, automation, targeted content, high rates of deliverability, integration with more than 70 services -- like WordPress, Shopify, and Sumo -- and excellent customer service are the reason I made it my go-to ESP. Whether you have a thousand subscribers or a million, whether you run a simple blog or a whole company, ConvertKit has a plan that's scaled to fit your budget and requirements. Go to ConvertKit.com/Tim to try it out and get your first month for free! Test the platform and make sure it works for you and your business. This podcast is also brought to you by WordPress, my go-to platform for 24/7-supported, zero downtime blogging, writing online, creating websites — everything! I love it to bits, and the lead developer, Matt Mullenweg, has appeared on this podcast many times. Whether for personal use or business, you’re in good company with WordPress — used by The New Yorker, Jay Z, FiveThirtyEight, TechCrunch, TED, CNN, and Time, just to name a few. A source at Google told me that WordPress offers “the best out-of-the-box SEO imaginable,” which is probably why it runs nearly 30% of the Internet. Go to WordPress.com/Tim to get 15% off your website today! *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews! For show notes and past guests, please visit tim.blog/podcast. Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Interested in sponsoring the podcast? Please fill out the form at tim.blog/sponsor. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss Instagram: instagram.com/timferriss Facebook: facebook.com/timferriss YouTube: youtube.com/timferriss Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Mike Maples, Jr.

Founding Partner

Floodgate