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“Rumi says you have to live life like it’s rigged in your favor.”

For Faisal Charania, that mindset is inseparable from his belief that small business in America is the best business in the world. As he puts it, small businesses generate ~70% of U.S. GDP, a level of economic diversification that every other country is trying—and failing—to replicate.

This episode explores how that conviction shaped Faisal’s journey from tax and M&A law back into the “holy game” of small business. Raised in a family-run Subway franchise, Faisal built elite legal skills only to return to entrepreneurship, founding Dogwood Brands Company in 2019. Today, Dogwood operates 60 locations across three states, employs roughly 300 people, and generates ~$20M in revenue across primarily asset-light retail service brands.

Faisal outlines Dogwood’s acquisition philosophy: hyper-fiscal conservatism, skepticism of EBITDA, and reliance on real indicators like revenue, taxes, rent, and labor ratios. He favors subscription models, creative deal structures, and mergers that align incentives rather than one-sided acquisitions.

Culture, he argues, is the CEO’s responsibility alone. By leading through personal sacrifice—flat compensation, frugal travel, and long-term thinking—Faisal views himself as a steward rather than an extractor of value. The true return on private equity, in his view, is the ability to change employees’ life trajectories for generations.

Drawing energy from Harvard Business School’s OPM experience and grounding himself in Stoic philosophy, Faisal emphasizes optimism, patience, and duty. The episode closes with a powerful reminder: leave it all on the field, embrace uncertainty, and trust that the journey itself is rigged in your favor.

Here are the Top 10 Takeaways from the conversation:

1. Live like it’s rigged in your favor
   Even setbacks compound positively with the right mindset.
2. Small business is America’s superpower
   ~70% of U.S. GDP comes from small businesses—pure economic diversification.
3. Hyperform fiscal conservatism wins
   Assume things will go wrong; trust revenue and taxes over EBITDA stories.
4. Structure beats valuation
   Earn-outs and mergers often outperform straight acquisitions.
5. Asset-light (or intentionally asset-heavy)
   Services win on efficiency; assets win when tax advantages are clear.
6. Subscriptions create durability
   Recurring revenue stabilizes growth and valuation.
7. Culture follows the owner
   Behavior, sacrifice, and consistency matter more than words.
8. People > profits
   The real impact is changing families’ long-term trajectories.
9. Patience on exits
   Franchise holds may extend to 8–9 years as cycles shift.
10. Leave it all on the field
    Live fully, save wisely, stay optimistic—fear ends when life does.

Books: A Day in the Life of Ivan Denisovich