Small Bets and Company of One

Last updated: August 19, 2025

I read Daniel Vasallo's Small Bets and Paul Jarvis's Company of One and found both making compelling points. They come at the same problem from different angles. Vasallo is about portfolio strategy for income experiments. Jarvis is about staying small on purpose. These ideas inform how I think about oddship and side projects in general.

Small Bets: the portfolio approach

Daniel Vasallo left a $500K/year position at AWS after eight years. Not because the money was bad, but because he noticed that external rewards (salary, promotions, status) had stopped being motivating. He wanted to "make a living with my own bare hands starting from nothing."

His first six months going independent, he tried building a traditional startup. It did not work. He pivoted to what he calls "small bets": quick, leveraged, stackable projects with big upsides and minimal cost.

The core ideas:

Portfolio over single bet. Instead of betting everything on one venture, create multiple small experiments where any single success can cover a hundred failures. This is not diversification for safety. It is a search strategy. You do not know in advance which idea will work, so you run many cheap experiments fast.

Time-boxing. Each bet gets a fixed time budget. Build something, ship it, see what happens. If it does not work, you have not lost much. If it does, you have the option (not obligation) to double down.

Leverage. Focus on digital products where marginal costs approach zero: courses, books, tools, communities. Vasallo built a Twitter course in 16 hours that generated $300K in revenue. His AWS book made $80K+ in five months. The Small Bets community itself (4,500+ members, lifetime access model) generates over $400K annually.

Survival orientation. Start with low-hanging fruit. Achieve small, steady wins. Build an audience before building products. Vasallo grew his Twitter following first, then created products for an audience that already existed.

The math is compelling. His revenue progression after leaving employment: -$74K (year one, investment), $209K (year two), $304K (year three), $336K (8.5 months into year four). Multiple independent streams, no single point of failure.

Company of One: staying small on purpose

Paul Jarvis spent 20 years building a career as a freelance web designer, working with clients ranging from startups to companies like Microsoft and Mercedes-Benz. His book argues that the fundamental assumption of business (growth is always good) is wrong.

The thesis: instead of growing bigger, focus on growing better.

The four traits: resilience (adapt to ups and downs), autonomy (independence from external resources), speed (quick implementation), simplicity (streamlined processes).

Upper bounds. Traditional goal-setting focuses on minimums. Jarvis argues you should also set upper bounds: the point where additional growth creates diminishing returns on profit or life satisfaction. This is counterintuitive in a culture that celebrates scale.

Minimum viable profit. Reach profitability as quickly as possible. Keep expenses minimal. Do not optimize for hypothetical future profits; focus on actual revenue from day one.

Relationship-based revenue. One of Jarvis's case studies: a training business that generates over $500K/year in profit using word-of-mouth marketing exclusively. The owner sends handwritten notes and chocolates ($20 investment per referral) to convert referrals into $2,000 training programs. No marketing department. No growth team. Just deep relationships.

The statistics are stark: 74% of high-growth tech startups fail due to premature scaling. Meanwhile, 86% of companies still active after eight years used no venture capital funding.

Where they overlap

Both frameworks reject growth-for-growth's-sake. Both prioritize lifestyle over valuation. Both prefer bootstrapping over external funding. Both treat autonomy as a non-negotiable.

The difference is emphasis. Vasallo is more experimental: run many projects in parallel, double down on winners. Jarvis is more focused: pick your thing, make it excellent, set limits. In practice, I use both. Small bets for discovery, company-of-one thinking for anything that sticks.

The oddship philosophy

oddship is where these frameworks become practice. It started as a vacation writing session in August 2025, turned into a website, and evolved into the umbrella for everything I build on the side.

The full manifestos live on the oddship about page. The short version: treat identity as something you rebuild while moving, not something you defend from a fixed position. Stay small on purpose. Document the work while it's still messy.

Principles I took away

Side projects deserve rigor. If you're going to build things on the side, treat them seriously: track them, set deadlines, ship. The small bets framework gives a structure for this: time-box, ship, evaluate, move on or double down.

Intrinsic motivation matters. Both authors emphasize that building things you care about sustains energy better than external validation alone. This is why I keep working on oddship even when there's no audience yet.

Portfolio over single bet. Most side projects won't work out. That's fine. The point is running enough low-cost experiments to find the ones that do.

Set upper bounds. Jarvis's idea of upper bounds, knowing when enough is enough, is underrated. Not everything needs to scale. Some things are better kept small on purpose.