Mark Grimes launched 31 startups in 31 days to find winners fast

Executive overview

Serial entrepreneur Mark Grimes, drawing on 31 years of founding experience and a backlog of 350+ ideas, spent August 2020 launching one new startup every single day — then gave himself 90 days to get as many as possible to cash-flow positive. His definition of "launch" is deliberately minimal: get the idea out of your head, put it in public, and start talking to potential customers — no business plan, no legal entity, no website required. The core insight is that a broad, public, low-cost exploration of many ideas simultaneously can surface winners faster than sequential focus, provided the founder keeps execution costs near zero and lets customer conversations determine which bets deserve more chips. All revenue and expenses are tracked publicly, and Grimes is explicit that cash-flow positive means real sales exceeding real costs — not a gimmick. At the time of recording he had 57 days left and reported being energised rather than exhausted.

Background and founding philosophy

• First company launched in 1989 targeting performing-arts marketing directors; cash-flow positive in under 30 days.
• Grown two companies to $7M+ revenue; largest was a 40-person interactive ad agency with offices in three cities.
• Angel investing alongside his wife: $25k–$100k per deal, roughly 15 years ago.
• Core discipline: compress costs to near zero at launch and secure paying customers before spending on infrastructure.
• Currently runs a 12-year-old co-working space in Portland and a startup-focused podcast network.
• Pandemic freed up time and pushed him to act on the long-running list of 350+ ideas he had been accumulating in a spreadsheet.

What counts as a launch — and what counts as cash-flow positive

• A launch = idea is out of your head, published publicly, and you are actively speaking to potential customers.
• No business plan, website, domain, or legal registration required on day one.
• Cash-flow positive = revenue greater than zero and greater than all expenses — no gaming with trivially cheap products.
• All 31 companies' financials tracked and published online so anyone can inspect them.
• The shotgun approach is intentional: if even a handful reach profitability, the experiment succeeds.
• Grimes refuses to write off any company until the final day of the 90-day window.

Example startups: axes, containers, cows, and whiskey

• Tillamook Axe Company sells precision-made axe-throwing targets built to World Axe Throwing League specs by a coastal Oregon woodworking couple; a companion podcast called "Axe Me Anything" will be sponsored by the company itself.
• Walden for Founders proposes a community of 12–15 founders living in high-end shipping containers (320–640 sq ft each) on the Oregon coast, targeting founders who have tired of accumulating things and want minimalist, relocatable community living.
• Cow Working invites a live dairy-farm camera feed into Zoom meetings for comic relief; three people had already asked for pricing at time of recording, inspired by an existing competitor called "Goat to Meeting."
• Whiskey Cones produces hand-blown high-end whiskey glasses, one maker trained by glass artist Dale Chihuly — Grimes's first physical-product venture after a career in services and software.
• Almost Quarantined is a 20th-anniversary event for the film "Almost Famous," featuring the real Penny Lane and editor Ben Fong Torres in a live Q&A.
• Roughly a third of the 31 ideas cluster around startups, founders, and entrepreneurship — reflecting his natural network — while the rest span unrelated consumer and niche markets.

Managing complexity across 31 simultaneous bets

• By day 10 Grimes questioned the decision; public commitment to the project was the main force that kept him going.
• Each new launch added compounding coordination overhead: by day 31 he had 60 days left and dozens of threads to manage.
• Kept himself sane by focusing on "the one thing that needs to happen next" for each company rather than trying to run full playbooks in parallel.
• Did not build teams in advance; instead invites followers to self-organise around individual ideas in exchange for a share of net revenue.
• Not making major capital outlays himself — finding partners (woodworkers, container builders, glassblowers) who contribute manufacturing in exchange for upside.
• Acknowledged the model is different from his normal deep-focus style: at 60 days in he was still only a few steps into most of the 31, whereas normally he would be deep into just one.

Why this approach — and what it reveals about idea validation

• Startup Weekend proves a 72-hour sprint can produce MVPs with revenue; 31-in-31 extends that logic to a month.
• A recently exited founder Grimes spoke with had tried 10 companies over a year, got three launched, then went all-in on one that became an 8-year success — confirming the pattern.
• Public building removes the temptation to polish; bad ideas get exposed faster when strangers can see them.
• The challenge exposes which ideas attract organic helpers, early customers, and supplier partners — a real signal that a sequential, private approach would not generate.
• Grimes is explicit that he expects most of the 31 to generate little or no revenue; one or two reaching sustainability is the realistic win.
• Audience revenue guesses ranged from a few thousand dollars to $1.75M total — showing the genuine uncertainty even sophisticated observers have about shotgun-portfolio outcomes.

Business heroes and philosophy

• Richard Branson: cited for 400+ Virgin companies, storytelling ability, and apparent enjoyment of life and social impact.
• Mohammed Yunus: microfinance pioneer Grimes has met in person; admired for social-change orientation.
• Seth Godin: worked together building Yoyodyne (pre-Yahoo acquisition) from 1996; Godin faxed Grimes after seeing his website, they collaborated four years remotely, and Grimes has never met him face to face.
• Common thread across all three: ability to entertain and tell stories as a core business skill, not a side trait.
• Grimes's message to the pandemic's 55 million newly unemployed: you need one idea, not a plan or funding — just start talking to customers.

Key lessons for founders

• Speed of iteration matters more than depth of preparation at the earliest stage.
• Writing ideas down in a spreadsheet preserves optionality; vague two-in-the-morning notes rarely survive re-reading.
• Physical products are an entirely new discipline for a services/software founder — supplier relationships replace internal capability.
• Keeping costs at zero is not just frugality; it is the mechanism that makes a 90-day cash-flow-positive deadline achievable.
• Doing the experiment publicly forces honesty, generates a built-in audience, and creates accountability that private projects lack.
• The definition of success should be set before the clock starts: here, cash-flow positive on real revenue, not vanity metrics.