From: myfirstmillionpod
Kevin Rose is an “internet OG” known for his prolific career as a founder, venture capitalist, and investor, consistently exploring diverse ventures and new technologies [00:00:38]. His career path, while appearing random, is unified by a “common thread of exploration” and a drive to build things that don’t yet exist but should [00:04:20] [00:04:43].
Early Entrepreneurship and Angel Investing
Rose began his entrepreneurial journey by creating Dig in 2004, which became one of the largest link aggregators and a cultural phenomenon during the Web 2.0 era, reaching 38 million monthly users at its peak in early 2006 [00:02:28] [00:02:33] [00:05:50]. While Dig didn’t turn out “as wonderful” as expected, it led him to build connections with future industry titans like Jack Dorsey, Evan Williams, and Mark Zuckerberg [00:02:52] [00:06:01].
His most financially successful endeavor has been the investment side of his career [00:06:21]. He started making small Angel investments, such as a $25,000 check into Twitter’s seed round and investments in Facebook, after selling a portion of his Dig stock [00:07:57] [00:08:02]. He made these investments because he believed in the potential of products like Twitter’s “following” model, which he thought would “blow up” if it caught on with celebrities [00:11:13] [00:11:32]. He also invested in Square after promoting an early prototype through a YouTube video, which helped him secure a spot in their seed round when an investor dropped out [00:12:51] [00:13:20].
His largest company sale as a founder was Revision3, a media company he co-founded, which was acquired by Discovery Channel’s digital arm for $35 million around 2008 [00:06:58] [00:07:10].
Hodinki: Content-to-Commerce Success
One notable venture is Hodinki, a watch blog that also sells watches [00:03:04]. Rose initially created Watchville, an aggregator app for watch content, driven by a personal passion for watches, especially inherited from his father [00:27:32] [00:27:39] [00:28:16]. Watchville brought together various sources and made them mobile-friendly, addressing a gap in the market [00:28:18] [00:28:22]. Recognizing Hodinki as the leading content source, he merged his company with theirs, becoming CEO [00:29:12] [00:29:17]. At the time of merger, Hodinki had about 2 million in annual revenue [00:29:31]. They then integrated e-commerce and established partnerships with major watch brands, growing the company to over $100 million in annual revenue [00:29:37] [00:31:11].
This success stemmed from a focus on high-quality, technically deep editorial content that built trust with readers [00:33:51]. When hiring writers, Rose prioritized individuals with a “natural organic built-in love” for horology and deep technical knowledge, even if their writing skills were initially B-plus, as editorial layers could refine the content [00:34:49] [00:35:25]. This model of trusted content leading to commerce is exemplified by Hodinki and Bring a Trailer (for cars) [00:34:01] [00:31:41].
Approach to Projects and Their Lifespan
Rose doesn’t have hard-set rules for when to kill a project [00:20:56]. Often, projects are discontinued if the initial market thesis or concept doesn’t gain traction [00:20:46]. However, he sometimes puts projects into “maintenance mode” if he believes the market isn’t mature enough, as was the case with his Zero fasting app, which saw slow but consistent growth before exploding when intermittent fasting became mainstream [00:21:41] [00:22:09]. Conversely, apps like Tiny, a photo-sharing app, were shut down quickly after an initial surge in downloads, as it became clear they were a “feature not a real product” [00:23:00] [00:23:07].
His motivation for starting businesses is never primarily financial; it’s always driven by personal passion, creativity, and the “exploration of an idea” [00:24:17] [00:24:46]. He finds the “blue ocean” aspect of the crypto and NFT world particularly exciting due to the vast opportunities for building [00:25:40] [00:26:09].
Investment Strategy
His personal investment portfolio, outside of venture capital, is “super vanilla,” primarily consisting of low-cost Vanguard index funds (about 80%) and a small percentage (around 10%) in crypto assets (50% NFTs, 50% digital assets) [01:22:50] [01:23:50] [01:23:58]. As a venture capital partner at True Ventures, he also invests a substantial percentage of his own money into the fund, considering it his high-risk bucket [01:21:51] [01:22:38]. He also recommends investing in I-bills (earning over 9%) due to their no-brainer scenario [01:23:20].
Insights on Startup Culture and Personal Growth
Rose values entrepreneurs who think about “entire new verticals” or “flipping something completely on its head” rather than just iterative improvements [00:37:29]. His approach to startup culture aligns with advice for startup founders from experts like Mark Zuckerberg, who emphasized surrounding oneself with smarter people and not being afraid to ask questions, a lesson Rose learned to embrace, particularly as a college dropout [01:15:16] [01:16:32] [01:17:01].
In recent years, Rose has focused on “mastering his own mind” and achieving personal peace, having experienced significant anxiety as a young entrepreneur constantly driven to win [00:38:55] [00:39:19]. This focus on mental well-being led him to create projects like the meditation app Oak and his Zero fasting app [00:39:26]. He aims to quiet his mind, a challenge he likens to Elon Musk’s inability to shut off constant thinking [00:40:01].
Future Interests: AI and Blockchain
Rose is “very bullish” on AI, believing it will “change everything” in the next five years [00:48:33] [00:50:32]. He foresees AI destroying the low end of the creative market and eventually moving up the chain, with tools already capable of creative writing and prompt-based art [00:48:51] [00:49:00]. He highlights how AI plugins in design tools like Figma are already streamlining interface creation, compressing the time to market for new ideas [00:51:41] [00:52:23]. He observes the flow of high-quality engineering talent moving into AI as a strong indicator of its potential [00:50:20] [00:50:25].
In the world of Web3, Rose’s project Proof curates NFTs with a strong editorial point of view, focusing on long-term value rather than quick flips [00:32:57]. While acknowledging the “dogmatic” and “silly” aspects of some Web3 maximalists who advocate for complete decentralization, he emphasizes the practical benefits of blockchain technology [00:58:16] [00:59:04]. He believes that most people will interact with NFTs without even realizing they are using blockchain technology, as it will be integrated seamlessly into apps and digital wallets [01:10:01].
He offers compelling use cases for NFTs beyond art:
- Proof of Provenance and Scarcity: NFTs provide verifiable provenance and scarcity, addressing issues like forgery in collectibles (e.g., high-end wine or luxury watches) [01:07:40] [01:13:01].
- Efficient Asset Transfer and Storage: NFTs can represent physical assets, allowing for easy transfer of ownership and ensuring optimal storage conditions without physical possession, eliminating fraud [01:13:40] [01:14:38].
- Loyalty and Rewards Programs: Blockchain can power transparent and permanent loyalty programs, such as artists rewarding fans based on concert attendance, ensuring that data persists even if a company fails [01:16:11] [01:17:00].
- Interoperability in Gaming: Digital in-game items represented as NFTs could be owned by users and transferred between different games, increasing their value and allowing players to recoup investments [01:18:11] [01:18:22] [01:18:41].
While acknowledging Bitcoin’s volatility and environmental concerns, he views it as a valuable asset class for diversification [01:20:15] [01:20:47].
Conclusion
Kevin Rose’s career epitomizes continuous evolution and exploration in the startup world. From early internet ventures to successful Angel investing and the innovative content-to-commerce model of Hodinki, he consistently seeks “blue ocean” opportunities and embraces new technologies. His personal journey, which includes a focus on mental well-being and a balanced investment philosophy, provides a unique perspective on building a successful startup and living a fulfilling life in the fast-paced tech industry.