This Week in Startups
This Week in Startups

E1044: Ask Jason! Starting a company in an economic crisis, bringing on & compensating startup advisors, scaling diligence as an angel investor, Jason’s thoughts on solving the unemployment surge & more!

0:01 Jason previews today's Ask Jason & drops some hints about the Super Secret TWiST Slack room 2:29 Aaron asks how investors view no-code startups 6:33 Andrii asks if an economic crisis is a good time to start a company 9:52 Jesse asks if he should start trying to raise a round of funding

Featured Speakers

Jason Calacanis HostJason Calacanis Guest

Topics Discussed

Episode Summary

Executive Summary: Jason Calacanis answers startup questions from the private TWIST Slack, arguing that no-code can speed early validation, crises are excellent times to start companies, investor outreach must be personalized, advisors should be paid with clear scope and equity, small angels should scale diligence to check size, cloud kitchens will expand dramatically, and post-crisis unemployment will be absorbed by entrepreneurs and the gig economy.

Main Topics: No-code startups and investor perception: Calacanis explains what no-code is, why it can improve speed and capital efficiency, and when a startup might need to move to custom code as scale or performance demands increase. Starting companies during an economic crisis: He argues downturns are ideal for founders because competition for talent, funding, and customers is lower and acquisition costs can fall sharply. Fundraising strategy in a downturn: He advises highly targeted, lightweight investor outreach with customized emails, strong metrics, and mini-processes rather than broad cold blasts. Advisors: why and how to use them: He outlines the purpose of advisors as reputation, network access, and practical expertise, and suggests compensation should reflect hours, value, and stage. Angel investing diligence for small checks: He says $5K angels should not impose heavy burdens on founders; diligence should be proportional and can rely on product use, reviews, and syndicate leads. Cloud kitchens and delivery economics: He predicts cloud kitchens will become a major, anti-fragile business model as consumer behavior shifts toward delivery and pickup. Unemployment, gig work, and economic recovery: He believes the gig economy and startup formation will absorb displaced workers, and that the crisis will accelerate entrepreneurial activity and market reallocation.

Key Arguments: No-code is a legitimate early-stage path because it lets founders build and learn quickly without overpaying for development. Investors will usually be impressed by no-code efficiency if it generates revenue and proves demand. A great time to start a company is during a downturn because competition for talent, funding, and customer attention is reduced. Fundraising in a crisis should be highly targeted and framed as a low-friction conversation with clear traction. Advisors should be brought in when their name or expertise materially helps with credibility, hiring, sales, or product strategy. Advisor compensation should be based on expected value: cash plus equity, or equity alone for high-profile names, with defined scope and monthly time expectations. Small angel investors should scale diligence to check size and use low-cost methods like using the product, reading reviews, and studying competitors. Cloud kitchens are positioned as a structural shift in food service, not just a real estate play, and should benefit from long-term adoption of delivery. The gig economy acts as a safety net and a labor-market pressure valve, improving worker optionality and wage competition. The crisis may accelerate the failure of weak companies and strengthen the best ones, improving talent reallocation and entrepreneurial recovery.

Data Points: TWIST Slack members: 3,200 - Size of the private startup community used for sourcing listener questions. Potential no-code user threshold for custom code: 10,000 to 100,000 users - He suggests some startups may need to move beyond no-code when scale or performance demands increase. Growth cited by founder Jesse: 90% month over month for 7 months - Example of strong traction used to discuss whether to raise capital in a downturn. Net monthly revenue cited by Jesse: $7,700 - Current revenue level for the marketplace startup considering fundraising. Laid-off salespeople referenced: 100,000 - Motivation for discussing fundraising and supporting workers during the crisis. Adviser consulting example: $2,000 per month / $24,000 per year - Illustrative market rate for a consultant who could help build a sales team. Equity ownership example for advisors: 50 bps to 1% - Suggested range for a high-profile advisor whose reputation adds credibility. Typical marketing spend range: 10% to 30% - He says many companies end up spending low double digits on marketing once product-market fit exists. Angel check size discussed: $5,000 or less - Used to explain how much diligence is appropriate for a tiny investment. Portfolio diversification threshold: 30 to 50 investments - He cites this as a rough range where venture power-law diversification begins to work. Cloud kitchens footprint example: 10,000 to 20,000 square feet - Describes the shared-kitchen model housing many brands in one facility. Cloud kitchen brand density example: 30 brands - Illustrates how many virtual restaurant brands can operate from one shared kitchen location. Job loss estimate discussed: 10% of the workforce / 20 million workers - Used in the unemployment discussion about pandemic-era layoffs and furloughs. Rehire assumption: 35% - Calacanis speculates roughly a third of furloughed workers may return to prior jobs.

Pivotal Quotes: "fortunes are built in the down market, they're collected in the up market." — Jason Calacanis: His core thesis on why recessions are ideal periods to found and invest in startups. "slow down to speed up." — Jason Calacanis: Advice on personalizing investor outreach and relationship-building rather than blasting cold emails. "A great time to be an investor in companies." — Jason Calacanis: His answer to whether an economic crisis is a good time to start a company.

Implications: Founders should use the downturn to validate cheaply, fundraise selectively, and lean into no-code and delivery-era business models. Investors should calibrate diligence and advisors by stage and check size, while workers may increasingly move into gig work or new startups.

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About This Week in Startups

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.

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