Legendary early-stage startup investor Mike Maples, Jr. shares insights on breakthrough startup ideas, the importance of thinking differently, avoiding comparison and conformity traps, storytelling, and healthy disagreeableness in startup success. He discusses applying pattern-breaking principles in large companies and offers advice for founders. Pre-order his book Pattern Breakers for more insights and learnings.

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 

In this engaging discussion, Mike Maples, Jr., co-founding partner of Floodgate and veteran investor behind major startups like Twitter and Twitch, delves into the essence of pattern-breaking entrepreneurship. He shares insights on embracing 'disagreeableness' as a vital trait for innovation, emphasizing the need for bold perspectives in pitching ideas. The conversation also touches on transforming limitations into opportunities, and the importance of aligning visions between founders and investors. Mike's groundbreaking ideas from his book, 'Pattern Breakers,' provide a fresh lens on the startup landscape.

"If the customer doesn't scream, you don't have product-market fit." — Andy RachleffWelcome 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. 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Venture capitalist Mike Maples, Jr. discusses spotting visionaries, missing out on Airbnb investment, AI future between incumbents and upstarts. Emphasizes startups reshaping market, non-consensus insights with AI, and importance of embracing failure for success.