Early Career Decisions and Entering Venture

I first found Mike Maples when I came across his podcast with Osman Rashid, (Cofounder of Chegg) about 6 years ago. I have since admired Mike’s philosophy on startups and investing. Mike is an early investor in category defining companies like Twitter, Okta, Chegg, Twitch, Clover Health and Applied Intuition to name a few.

I hosted a dinner on the topic of technological stagnation about 3 years ago with Mike and a few other investors and founders, this was pre-ChatGPT, before defense or dual-use investing went mainstream and before reindustrialization became a national agenda for the US.

We look back at what has changed in the last few years and if we are making progress at a better rate in the world of atoms than before. In one way, Mike has seeded the reindustrialization movement by investing in Chris Power, Cofounder of Hadrian (which was the only investment he made in 2021) and key orchestrator of the marquee Reindustrialize Conference in Detroit which is leading the way on building a platform for policymakers, startups, capital allocators and manufacturers on bringing back the most critical industries through advanced technology adoption.

In this episode, Mike talks about how startups have to build a radically different future and through great storytelling bring their customers, investors and employees to their version of the future which they are already convinced of. I also asked him about the origin stories of investing in and finding Twitter, Digg and Lyft.

We also discuss how Floodgate differentiated itself in 2015 when they were a decade into seed investing and again in 2025 two decades into seed investing. Floodgate has a concentrated investing strategy and having been around for 20 years, they are unique in the sense that they were not tempted to go raise a mega fund and maintain a fund size of around $150m and do only seed.

I really enjoyed spending a couple of hours with Mike, I hope y’all enjoy this one.

One of my favorite quotes from the episode among gems Mike dropped:

Even being different worse is better sometimes than being better at the same (thing). - Mike Maples Jr.

Special thanks to NFX for hosting us for this episode.

Watch on YouTube:

Timestamps:0:00 - Introduction02:32 - Technological stagnation and are we on track to build the Jetson’s future? 10:46 - Startups avoid the comparison game and why the best founders are great storytellers19:00 - The insight is the magic and the breakthrough mechanism 26:44 - Is founding companies art or science? 30:21 - Funding talent in pursuit of interests39:49 - Story of investing in Qasar Younis of Applied Intuition 45:00 - How Floodgate is different and reinventing itself now51:00 - Founder archetypes that fit the Floodgate thesis58:46 - “Disagreeableness” as a skill in founders 1:08:56 - Decisions that compounded 1:19:11 - Learning from legendary founders and early investment stories1:33:00 - Being your own personal monopoly 1:37:03 - Non Consensus Investing 1:47:11 - Why write Pattern Breakers?1:51:19 - Advantage of smaller funds 1:59:45 - Favorite books, TV shows, movies

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