Conventional wisdom to 'stay focused' is flawed. Breakthrough growth often comes from making many small, exploratory bets. YipitData's success wasn't from perfecting one thing, but from the one small, tangential bet each year that drove 90% of the growth while others failed.

Bridge was founded just before the 2022 crypto crashes. The collapse of the NFT market, their initial focus, forced them to pivot to stablecoin infrastructure, which proved to be a much larger and more durable market, demonstrating how market shocks can be clarifying.

A company with modest growth experimented with niche content for a small user segment, revealing a massive, underserved market. This led to a second, separate app that quickly surpassed the original product's revenue and drove hyper-growth, challenging the "focus on one thing" dogma.

Counter to the "niche down" mantra, Missive's horizontal approach became a key strength. With their largest customer segment representing only 6% of revenue, they are highly insulated from industry-specific downturns. This broad, long-tail customer base provides a stable and defensible foundation.

The key to effective portfolio entrepreneurship isn't random diversification. It's about serving the same customer segment across multiple products. This creates a cohesive ecosystem where each new offering benefits from compounding knowledge and trust, making many things feel like one thing.

Front Office Sports intentionally diversified from 90% reliance on newsletters to a healthier model where newsletters, social media, and events each contribute significantly (roughly 30%, 30%, and 20%). This balanced, multi-pillar revenue strategy makes the business more resilient, scalable, and valuable.

When COVID-19 invalidated its revenue plan, Nextdoor's GM used a pre-existing worst-case scenario to pivot the product strategy. The focus shifted from subscriptions to features that provided immediate cash flow to local businesses (e.g., gift cards), enabling a quick, board-aligned response to the crisis.

Relying on one signature offer or income stream is a high-risk strategy. A more sustainable approach is building a portfolio business with multiple, smaller streams—like a course, a membership, and affiliate income. This ecosystem creates stability, allowing the business to weather storms and reducing pressure on any single component.

Contrary to the trend of specialized 'monoline' companies, Aviva's CEO asserts that diversification offers significant capital benefits. It also allows for the efficient scaling of major investments, like generative AI, across numerous product lines—a strategy that has proven more resilient and successful over the last five years.