Mike Maples

This Week In Startups is made possible by: CLA - www.claconnect.com/withyou Northwest Registered Agent - www.northwestregisteredagent.com/twist Agree.com - www.agree.com Today's show: Forget the triple-triple-double-double-double; the new bar for startups hoping to raise venture capital has reached the stratosphere, though our venture panel is worried that startups are focusing too much on today's problems that may not become companies tomorrow. During a lively VC roundtable, Cowboy's Aileen Lee, Floodgate's Mike Maples, and Lerer Hippeau's Ben Lerer joined Alex to dig into exiting pre-AI startups, rising valuations, token spend, why they are keeping their funds small, and whether the government just tripped OpenAI and Anthropic! Guest Links: Aileen Lee https://x.com/aileenlee Cowboy VC https://cowboy.vc Mike Maples https://x.com/m2jr Floodgate https://www.floodgate.com Bene Lerer https://www.linkedin.com/in/benjlerer Lere Hippeau https://www.lererhippeau.com Timestamps: 0:00 Aileen Lee, Mike Maples, and Ben Lerer join the show 5:13 Venture liquidity returns: what SpaceX/Stripe distributions mean for LPs 9:13 Bending Spoons prices IPO at $29/share, roughly $18.4B valuation 10:31 Agree.com - Stop chasing invoices and automate your entire contract-to-cash stack. Go to https://agree.com and tell them Jason sent you to get 50% off for life! 12:09 "Companies get bought, not sold" — Ben on taking first offers seriously 17:41 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off! 19:34 Mutiny's burn-the-boats AI pivot with Jaleh Rezaei 20:19 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://www.northwestregisteredagent.com/twist 22:15 Mike's KeepSafe story: the "rule of 70" and profit-first companies 25:12 The new growth bar: 5x, 4x replaces triple-triple-double-double 28:55 Fund size is your strategy: why Floodgate and Lerer Hippeau stay small 30:11 CLA - Innovation takes balance. CLA's CPAs, consultants, and wealth advisors can help you get from startup to where you want to end up. Get started now at https://www.claconnect.com/withyou 37:39 The $100M Series A: Starcloud, General Intuition, Scale Cognition, Scout AI 40:35 King-making rounds and why mega-seeds destroy optionality 54:11 Open-weight models: the GLM-5.2 moment and going model-agnostic 55:30 Why fine-tuning open models is a treadmill, with Cursor/Kimi as an example 1:03:28 Grading the Trump administration on Mythos and Fable 1:06:33 Rising anti-AI sentiment, the wealth gap, and lessons from social media 1:11:43 Raising kids in the post-intelligence era 1:12:35 Where to find the panel and what each firm is investing in Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com

Aileen Lee

Partner

Cowboy Ventures

Mike Maples

Co-Founding Partner

Floodgate

Ben Lerer

Managing Partner

Lerer Hippeau

Mike Maples is one of the OG seed investors of the last two decades. As a co-founding Partner at Floodgate, Mike has been on the Forbes Midas List eight times in the last decade. Some of Mike's investments include Twitter, Twitch.tv, Clover Health, Okta, Outreach, Chegg, Demandforce, and Applied Intuition. In Today's Episode with Mike Maples We Discuss: 04:02 Does Seed Even Make Sense as an Asset Class? 05:16 Fund Size and Strategy: How to Do a 10x Fund? 08:12 Follow-On Investments: Are they BS? 16:41 Finding Inefficiencies in the Market 26:31 Exit Strategies and Liquidity Events: When to Sell? 35:14 How Floodgate Lost Billions Missing Airbnb and Pinterest 35:43 3 Frameworks for Evaluating Startups 36:23 Case Studies: Zoom and Okta 43:34 How to Truly Analyse Product-Market Fit 45:22 Challenges with Overfunding Startups 50:02 2024 in Review: Company and Fund of the Year 54:25 Predictions for 2025

Mike Maples

Co-Founding Partner

Floodgate

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 the future of venture capital may look like over the next decade - here are a few favorite takeaways on what makes outstanding startups from one of the industry's most influential names. (00:00) Intro (01:12) Meet Mike Maples: Venture Capital Icon (04:20) The Genesis of Twitch and Startup Pivots (07:51) Understanding Inflections in Startups (14:38) The Role of Insights and Ideas in Startup Success (22:13) The Importance of Movements and Founder-Future Fit (26:10) Case Studies: Quibi, Tesla, and More (43:41) The Trap of Mundane Startup Ideas (45:36) The Inflection Stress Test for Startups (47:06) The Twitter Success Story (52:40) The Rise of Seed Funding (56:55) Traits of Successful Founders (59:39) The Importance of Storytelling in Startups (01:05:47) Navigating the Challenges of Disruptive Startups (01:08:31) Reflections on Early Investment Decisions (01:13:57) Entering the Venture Capital World (01:20:25) The Evolution of the Tech Industry (01:22:47) Reflecting on the Dot-Com Era (01:23:06) The Evolution of Cognition and AI (01:24:03) Investment Strategies and Market Trends (01:25:56) The AI and Dot-Com Bubble Comparison (01:33:46) The Rise of Bitcoin and Crypto (01:37:02) Navigating Venture Capital Cycles (01:49:57) Advice for Aspiring Investors (01:54:09) The Importance of Authenticity and Specialization (02:03:20) Closing Thoughts and Reflections Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Mike Maples

Co-Founding Partner

Floodgate

Eric Paley is the Managing Partner at Founder Collective, one of the world's most successful seed funds with investments in the likes of Uber, The Trade Desk, Coupang and Airtable. Mike Maples is one of the OGs of seed investing. As the Co-Founder of Floodgate, he has backed the likes of Twitch, Okta, Lyft, Twitter and more. Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds with a portfolio including Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. In Today's Episode on Is the Venture Model Broken? : Is the classic seed model dead? Can seed funds play in a world of $25M valuations? Why is having a firm grasp of the present the best thing an early-stage investor can have? Why does Mike Maples believe no company with true product-market-fit has ever failed? Why does Eric Paley believe "go faster" is the worst startup advice? Why does Mike Maples believe there is a direct relationship between price and risk? Why does Mike Maples believe that outliers by their very nature are lower priced? Why does Eric Paley not focus on ownership? Why can it be dangerous? What are the biggest risks for founders raising at valuations that are too high? Why does Eric Paley believe we will have the biggest chasm between TVPI and DPI in the prior vintage of venture capital returns? Why does Eric believe the majority of SPACs were BS and great companies can always go public? Why does Jason believe that if multiples do not reflate, the venture model is broken? Why does Jason believe we will see the biggest hiring spree in tech next year? How has illiquidity allowed Eric Paley to make some of the best investment decisions? What is Mike Maples biggest lesson from selling Twitter stock early at $1BN?

Eric Paley

Managing Partner

Founder Collective

Mike Maples

Co-Founding Partner

Floodgate

Jason Lemkin

Founder

SaaStrStorm Ventures

Mike Maples is one of the OGs of seed investing. As the Co-Founder of Floodgate, he has backed the likes of Twitch, Okta, Lyft, Twitter and more. Mike has been on the Forbes Midas List eight times in the last decade and was also named a "Rising Star" by FORTUNE and profiled by Harvard Business School for his lifetime contributions to entrepreneurship. In Today's Episode with Mike Maples We Discuss 1.) Lesson from SVB #1: The Importance of Scenario Planning: What is the right way to do scenario planning in startups? What is the difference between good vs bad scenario planning? What do the best scenario plans include and involve? What is the right way to communicate these scenario plans to your stakeholders? 2.) Lesson from SVB #2: The Importance of Financial Agility: What does it mean for a startup to be "financially agile"? From a banking relationships perspective, what can startups do to be financially agile? How many accounts should a startup have? How much runway should be in each? Should startups bank with startup banks as well as traditional banks? Should startups have their money in sweep accounts and money market accounts? 3.) Lesson from SVB #3: How to Master Crisis Communications: Why is it so important for founder to over-communicate in tough times? How transparent should they be in these communications? What does Mike mean when he says "be radically human"? If Mike were to face a crisis, what would he do differently in the way he communicates to his LPs? 4.) Lessons from SVB: The Wider World: Why does Mike believe the level of quantitative easing that occurred in COVID was scandalous? Does Mike believe the USD will continue to be the reserve currency of the world? Will we be in a better or worse macro situation by the end of the year? Has Mike ever had a company that achieved true PMF and failed?

Mike Maples

Co-Founding Partner

Floodgate

Shaan (@ShaanVP) and Sam (@TheSamParr) talk with seed VC Mike Maples (@m2jr). Mike is a co-founding Partner at Floodgate. He has been on the Forbes Midas List eight times in the last decade due to notable investments like Twitter, Twitch, Lyft, and Okta. In this episode he talks about the four big trends he is excited about, the types of companies he likes to invest in, and why a startup isn’t a company. He shares a few of the mental models he uses at Floodgate to evaluate startups and shares the thoughts behind some of his unique turns of phrase. --------- * Want to be featured in a future episode? Drop your question/comment/criticism/love here: https://www.mfmpod.com/p/hotline/ * Support the pod by spreading the word, become a referrer here: https://refer.fm/million * Have you joined our private Facebook group yet? Go to https://www.facebook.com/groups/ourfirstmillion and join thousands of other entrepreneurs and founders scheming up ideas. --------- Show notes: * (1:02) – Debrief of the episode * (6:37) - Intro to Mike Maples * (9:02) - How Mike thinks about the next big thing * (11:00) – The 4 inflections Mike is excited about * (13:51) – Cloud Offices * (19:33) – A brief history of centralization & decentralization * (22:48) – Examples of software defined companies * (26:14) – A practical way to prepare for the future * (30:23) – How Mike thinks about investing in startups * (33:07) – Startup investing mental models * (37:39) – Mike’s take on "1 to n" businesses * (42:36) – Mike on Balaji * (47:11) – Mike on media companies  * (49:49) – Force a choice, not a comparison * (54:46) – Mike’s information diet * (57:40) – Contact info & future topics

Mike Maples

Co-Founding Partner

Floodgate

Mike Maples is a Founder & Partner @ Floodgate, one of the leading early-stage firms of the last decade with investments in the likes of Lyft, Twitch, Twitter, Okta and Sonos to name a few. He has been on the Forbes Midas List since 2010 and was also named one of "8 Rising Stars" by FORTUNE Magazine. Before becoming a full-time investor, Mike was involved as a founder and operating executive at back-to-back startup IPOs, including Tivoli Systems (IPO TIVS, acquired by IBM) and Motive (IPO MOTV, acquired by Alcatel-Lucent.) In Today's Episode You Will Learn: 1.) How Mike made his way from founding startups to entering the world of venture and the gap he saw in the market when founding Floodgate? 2.) Mike has previously said, "a startup is not a company, it is a series of breakthroughs". How does Mike define a breakthrough? What are the 2 most meaningful breakthroughs a startup can experience? Which excites Mike the most to see? How do the best startups scale pre-breakthrough to post-breakthrough? 3.) What are the core ways inflections can create breakthrough opportunities? What were Mike's learnings on inflections from investing in Lyft? What does Mike mean when he talks about the importance of "backcasting"? What did investing in Twitch teach Mike about forecasting? 4.) How does Mike feel about the rise of operator and angel funds? How does Mike analyse the re-entrance of large multi-stage funds back into seed markets? Does Mike agree with Semil Shah, "founders are voting with their feet and taking multi-stage money at seed"? 5.) As Mike's peers have all moved into larger funds, Mike did not, why? How does Mike view "fund size as your strategy"? How does Mike think about the centrality of ownership? Does Mike really believe you can concentrate capital into your winners? What are the challenges? Why does Mike feel self-promotion is one of the biggest challenges in VC? Items Mentioned In Today's Show: Mike's Fave Book: Superforecasting: The Art and Science of Prediction Mike's Most Recent Investment: CommonStock As always you can follow Harry, The Twenty Minute VC and Mike and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mike Maples

Co-Founding Partner

Floodgate

Mike Maples is a Founding Partner @ Floodgate, one of the leading early-stage venture funds in the valley. Mike has made investments in the likes of Twitter, Twitch.tv, Weebly, Chegg, Bazaarvoice, Okta, and Demandforce. As a result, Mike has been on the Forbes Midas List since 2010 and was also named one of "8 Rising Stars" by FORTUNE Magazine. Before becoming a full-time investor, Mike was involved as a founder and operating executive at back-to-back startup IPOs, including Tivoli Systems (acquired by IBM) and Motive (acquired by Alcatel-Lucent.) In Today's Episode You Will Learn: 1.) How Mike made his way into VC and came to found Floodgate? 2.) How did the investment decision-making process change for Mike with the institutionalisation and fiduciary responsibility of an LP backed fund? 3.) How does Mike approach team building with Floodgate? What does he look for in his partners? What do most funds do wrong when hiring and expanding their team? 4.) Mike has a very different way of reading product and the associated market. What does Mike mean by saying the 'dance of product market fit'? Who leads what? How do they work together? What are the reasons startups do not achieve PMF? 5.) How does Mike assess the aspect of category creation? What are the fundamentals required to be a category king? What characteristics do category kings have? Items Mentioned In Today's Show: Mike's Fave Book: The Top 5 Regrets of The Dying Mike's Most Recent Investment: Dispatcher As always you can follow Harry, The Twenty Minute VC and Mike on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Angelloop is the leading post funding management platform for private market investors and their portfolio companies. They help investors manage and track their portfolio companies on the cloud while providing them with access to their investments performance data. Angelloop helps founders of startups track their performance, manage their cap table and keep their investors in the loop. Investors get free access while their portfolio companies pay only $49/Month. Use or share the promo-code 20MinVC to get your portfolio companies online with a two month trial. I'd like to thank Wealthfront for sponsoring today's podcast. Wealthfront are financial advisors that can help you invest your hard-earned dollars. Wealthfront's modern financial services helps tailor plans specifically for you, making it easy to reach your financial goals. Wealthfront has low fees and no trading commissions… It's financial advice at a fraction of the cost of a traditional advisor, all online. And if you sign up using my URL, you'll get your first $15,000 managed for free. Go to Wealthfront.com/20vc.

Mike Maples

Co-Founding Partner

Floodgate