Mike Maples Jr.

Background

Mike Maples Jr. is a co-founding partner of Floodgate, one of Silicon Valley’s pioneering seed-stage venture capital firms ¹. Maples established the firm as Maples Investments in 2006; Ann Miura-Ko joined as co-founding partner in 2008 ². The firm was renamed Floodgate Fund in March 2010 ². Floodgate’s first fund was $15 million, and the firm has since raised eight funds, including a $146 million seventh fund closed in October 2021 ³⁴.

Maples grew up immersed in the tech industry. His father, Mike Maples Sr., was an executive at IBM for two decades before joining Microsoft in 1988 as Executive Vice President of the Worldwide Products Group, where he reported directly to Bill Gates and was instrumental in developing Microsoft Office ⁵. The younger Maples describes himself as “a child of the PC revolution,” having written video games for the original Apple II and IBM PC in high school ³.

Maples earned a BS in Engineering from Stanford University and an MBA from Harvard Business School (Class of 1994) ¹³. His first professional role was as a Product Manager at Silicon Graphics (1990-1992), before attending HBS ⁶.

Before becoming a full-time investor, Maples was involved as a founder and operating executive at back-to-back startup IPOs ¹: - Tivoli Systems: Director of Product Marketing (1994-1997). The company went public (IPO: TIVS) and was acquired by IBM ¹. - Motive Communications: Co-Founder and Chief Marketing Officer (1997-2005). The Austin-based broadband management software firm went public in 2004 (IPO: MOTV) and was later acquired by Alcatel-Lucent in 2007 ¹³.

He has been named to the Forbes Midas List eight times in the past decade and was designated a “Rising Star” by Fortune ¹. He has also been profiled by Harvard Business School for his lifetime contributions to entrepreneurship ³. Steve Blank has called his book “the most important book on startups in the last ten years” ⁷.

In 2024, Maples published the national bestselling book Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Stanford Lecturer Peter Ziebelman ⁷. He also hosts the Pattern Breakers podcast (previously called Starting Greatness), featuring interviews with entrepreneurs including Marc Andreessen, Reid Hoffman, Kevin Systrom, Mark Cuban, and Tobi Lutke ⁸.

Stated Thesis

(Self-reported: These represent what Maples says publicly about his approach. See Inferred Thesis for analysis of actual investment behavior.)

Mike Maples has been one of the most publicly articulate seed investors about his investing framework. His core thesis centers on several interlocking concepts:

• Thunder Lizards: Maples coined this term – a metaphor derived from Godzilla – to describe “the tiny number of truly exceptional companies that are wildly disruptive capitalist mutations” ¹. He says: “Our job is to spot radioactive atomic eggs” – early-stage ventures with transformative potential ⁹.

• Inflections and Insights: His investment framework rests on two pillars. Inflections are external shifts in technology or society that create conditions for radical change. Insights are a founder’s unique understanding of how to harness an inflection to enable a different future ¹⁰. “A powerful inflection is a precondition of success in a startup” ¹¹.

• Pattern-breaking over pattern-matching: Maples explicitly rejects conventional VC pattern matching: “My job is to invest in pattern breakers… find the people who propose a new way” ¹¹. He argues the greatest startups break existing patterns rather than fit known categories ⁷.

• Founder-future fit: Rather than founder-market fit, Maples emphasizes whether the founder has a unique relationship with a future that others cannot yet see. He prioritizes founders who “live in the future – acting as if another world exists” ¹².

• Non-consensus and right: He seeks investments where the prevailing view is skepticism: “When a seed round is priced at $20M post, it’s not non-consensus. It’s priced to perfection” ¹³. His business model: “My business isn’t about how often I lose, but the magnitude of the rightness when I win” ¹³.

• Falsification over validation: Maples notes that approximately 80% of Floodgate’s exit profits came from companies that executed major pivots (including Twitter, Twitch, and Chegg), leading him to emphasize the quality of founder insight over initial product: “I’m not evaluating a product, I’m evaluating insights, inflections, and the capability of the founders to change the future” ¹²¹³.

• Living in the future: He frequently references William Gibson’s quote that “the future is already here, it’s just not evenly distributed” and looks for founders who are building from that vantage point: “If you’re living in the future and you notice what’s missing, your intuition about what to build is far more likely to be right” ¹⁰.

Inferred Thesis

Based on analysis of 46 verified investments in the table below and Floodgate’s 247+ total portfolio companies ²⁰:

Stage focus: - Predominantly seed-stage investments, consistent with the firm’s stated focus ¹ - Occasional Series A/B follow-on or co-investment ⁶

Sector concentration (of 46 verified investments): - Enterprise SaaS & infrastructure: 13 companies (30%) – including Okta, Outreach, Spiceworks, SnapLogic, Egnyte, Pantheon, Xamarin, Demandforce, Bazaarvoice, TextIQ, Lob, Sharethrough, LTSE ¹¹⁴ - Consumer & social: 10 companies (23%) – including Twitter, Chegg, Digg, Weebly, Refinery29, Mighty Networks, Smule, IFTTT, BranchOut, Milk Inc. ¹¹⁴ - AI & machine learning: 3 companies (7%) – Hebbia, Applied Intuition, SmarterDx ¹⁴ - Marketplaces & commerce: 5 companies (11%) – Lyft, Rappi, TaskRabbit, BigCommerce, The Zebra ¹¹⁴ - Healthcare: 2 companies (5%) – Clover Health, SmarterDx ¹¹⁴ - Climate & energy: 3 companies (7%) – Terradot, Living Carbon, OhmConnect ¹⁴ - Manufacturing & defense: 1 company (2%) – Hadrian ¹⁴ - Education: 4 companies (9%) – Clever, Thinkful, MissionU, LabDoor ¹⁴ - Gaming: 2 companies (5%) – ngmoco, Gowalla ¹² - Other (storage, seasteading): 2 companies (5%) – SpareFoot, Blueseed ²

Note: Some companies span multiple categories (e.g., SmarterDx is both AI and healthcare; Applied Intuition is both AI and autonomous vehicles). Totals may exceed 44 due to overlap.

Geography: - Heavily concentrated in the San Francisco Bay Area / Silicon Valley ¹ - Some presence in other US tech hubs, notably Austin, TX (Maples’ home market from his Motive Communications days) ³ - Select international investments, including Latin America (Rappi – Colombia) ¹

Typical check size: - Overall range: $100K-$5M ⁶ - Sweet spot: ~$2.5M ⁶ - Early Floodgate funds (2006-2012): $150K-$1M initial checks ² - Later, larger funds: $500K-$5M initial checks ¹²

Fund sizes (progression): - Fund I (2006): $15M ³ - Fund III: $73.5M ⁴ - Fund IV: $75M ⁴ - Fund V: $76M ⁴ - Fund VI: $131M ⁴ - Fund VII (2021): $146M ⁴

Co-investor patterns: - Frequent co-investor: Ann Miura-Ko (Floodgate co-founder) ¹ - Strong syndicate relationships with later-stage firms including Andreessen Horowitz (co-invested in Okta), Benchmark, and Sequoia, who often lead follow-on rounds ⁹¹⁵ - Generally invests alongside other angels or venture capital firms ² - Current Floodgate team includes Arjun Chopra (General Partner), Iris Choi (Partner), Jay Kennedy, and Leeor Mushin ⁶

Rather than participating in formal fundraising processes, Floodgate invests time upfront to get to know potential founders, ideating with them and sharing mental models. When a founder decides to launch their company, Floodgate offers terms early before they launch a process ¹⁴.

Notable patterns: - Strong affinity for companies initially dismissed or misunderstood (Twitter was seen as trivial; Lyft faced regulatory skepticism) ⁹ - Long hold periods – patience for “thunder lizard” outcomes rather than early liquidity ¹ - The firm positions itself as “Your First True Believers” and invests time upfront ideating with founders before they launch a formal fundraising process ¹⁴

Portfolio

This is a partial list. Floodgate has invested in 247+ companies, with 7 unicorns in the portfolio ²⁰. Years are approximate based on company founding dates and public records.

In Their Own Words

“You can’t achieve outsized results in life by doing things that others do – you have to do radically different things.” – Mike Maples Jr., Venture Almanac ¹³

“The seed investors that are rewarded most are not the futurists who can predict. They’re the ones who notice.” – Mike Maples Jr., The Generalist ¹⁷

“Don’t label startups. The moment you call something ‘Uber for X,’ you lose too much resolution to see what’s truly different.” – Mike Maples Jr., The Generalist ¹⁷

“A startup is a provocative act. By definition, a breakthrough startup says, ‘the present isn’t as good as it could be.’” – Mike Maples Jr., Outlander VC interview ¹¹

“A great startup idea forces a choice and not a comparison.” – Mike Maples Jr., Outlander VC interview ¹¹

“80% of our profits had come from what’s called pivots.” – Mike Maples Jr., Thought Economics interview, referencing Twitch, Twitter, and Chegg all having started as different businesses ¹⁸

“Timing may be the single most important factor, at least as it relates to the uncertainty of it all.” – Mike Maples Jr., Thought Economics interview ¹⁸

“Early customers are animated by belief, not utility. They buy for aesthetic reasons, not practical ones.” – Mike Maples Jr., Thought Economics interview ¹⁸

“You want to make everyone you persuade a hero in their own hero’s journey. The founder isn’t the hero; the founder is the mentor.” – Mike Maples Jr., Thought Economics interview ¹⁸

“Seed stage startup teams should look like a collaborative, improv jazz band, not a structured orchestra with sheet music.” – Mike Maples Jr., Venture Almanac ¹³

“If you’re a seed fund and you don’t have an explicit strategy to get into one of the top 20 seed rounds of the year, you don’t have a business.” – Mike Maples Jr., Venture Almanac ¹³

“The mission of the breakthrough requires the courage to be disliked.” – Mike Maples Jr., Venture Almanac ¹³

“The best way to compete is to choose not to.” – Mike Maples Jr., Tren Griffin interview ⁹

“Great companies happen because of great founders, not because of where they are or who the VCs are or any of that nonsense.” – Mike Maples Jr., Tren Griffin interview ⁹

Regarding the Twitter investment: When Evan Williams first described Twitter to Maples, he said users would write what they’re doing in 140 characters or less with “nothing” happening after. When asked about the roadmap and revenue model, Williams replied there was none, but explained that since a million people wrote blogs after he created Blogger, he figured he could get 10 million people to write micro-blogs. Maples invested. ¹⁶

Maples describes how Evan Williams and Kevin Rose gave him his first chance as an investor, taking a leap of faith and putting him in business. Maples notes that he tries to treat entrepreneurs with the same grace that Evan Williams offered him. ¹⁶

“I will always be grateful that some of the very best founders gave me the chance to be an investor and co-conspirator.” – Mike Maples Jr. ¹⁹

What Founders Say

“Mike Maples is an amazing VC and partner to Sharethrough. I wouldn’t be where I am now without Mike’s support and mentorship. If you ever have the opportunity to meet him, take it. I guarantee you will learn something profound.” – Dan Greenberg, CEO of Sharethrough ⁶

Tim Ferriss has called Maples “the man who taught me how to invest” and described him as “one of my favorite people and a personal mentor,” dedicating an entire episode of The Tim Ferriss Show (Episode #286) to Maples’ investing approach and worldview. ²¹

Note: Relatively few direct founder-about-investor quotes are publicly available for Maples. This section will be updated as additional testimonials are identified. Maples has described Applied Intuition co-founders Qasar Younis and Peter Ludwig as “among the best founders I had ever encountered,” but that is his characterization of them rather than a founder quote about him ¹.

Sources