Episode Summary
Executive Summary: Jason Calacanis answers community questions on startup challenges during COVID-19, sharing insights on sourcing talent for bootstrapped startups, building remote culture, marketplace strategies, pricing, and investor perspectives. He emphasizes the importance of timing, accountability, and community building through Slack.
Main Topics: Sourcing talent during a crisis (Priority: 5/5): Jason advises bootstrapped startups to offer equity, personalize outreach on LinkedIn, and treat hiring as a numbers game with 50+ hours per hire. Building remote culture (Priority: 5/5): Jason shares experiments like book clubs, 'small wins' Slack channels, and fun Zoom activities (e.g., hat contests, kids on calls) to foster connection and culture remotely. Marketplace building: supply first (Priority: 4/5): Jason explains the need to seed supply (e.g., paying for drivers, faking accounts) and limit geography or product segments to reach critical mass quickly. Pricing strategy and free trials (Priority: 4/5): Jason advocates charging early to validate value, avoiding free trials, and keeping pricing simple—citing examples like Netflix and criticizing complex pricing from newspapers. Investing in distributed startups (Priority: 3/5): Jason notes that investors increasingly care about results over office space, and distributed teams can use Zoom breakout rooms to impress VCs efficiently. Government regulation and marketplaces (Priority: 3/5): Jason criticizes San Francisco's cap on delivery fees, arguing the free market (e.g., restaurants building their own apps) naturally corrects excessive charges. Timing and resilience (Priority: 3/5): Jason stresses that timing is critical but persistence matters more—using Netflix and Marvel as examples of companies that succeeded by not quitting.
Key Arguments: Hiring requires personalized outreach and treating it as a funnel; generic emails are easily ignored. Remote culture needs intentional rituals like book clubs, small wins sharing, and fun Zoom traditions. Free trials lead to low commitment; charging early proves product value and filters bargain hunters. Government should not cap delivery fees; competition naturally prevents price gouging. Investors prioritize results over physical offices; distributed teams can use Zoom's breakout rooms for efficient team introductions. Marketplaces must supply first (e.g., Airbnb, Uber) by seeding inventory and limiting scope. CEO motivation relies on defining 'okay, good, great' outcomes and trusting but verifying team efforts.
Data Points: Slack community members: 11,000 - Crossed 11,000 members in under two weeks, ~5% of podcast audience. Banned users from Slack: 20 - Jason personally banned 20 spammers since starting the Slack. Time spent per hire: 50-150 hours - Jason recommends putting at least 50-150 hours into each hire. Remote team meeting suggestion: 25 bucks per person - Jason spent $25 per person on lunches during a remote CEO lunch to foster culture. Angel University attendance goal: 250 people - Jason set a goal of 250 attendees for Angel University, achieved via retargeting and emails. Savings from SenPro Online: 5 cents per letter, 40% off Priority Mail - Mentioned in a sponsored segment about Pitney Bose's service.
Pivotal Quotes: "If you talk about me in your email, as opposed to talking about yourself, you're going to get much further and a much higher response rate." — Jason Calacanis: Advice on personalized outreach for hiring and networking. "The free market works... If you take too much, the take-rate is too much, then people will stop electing to be part of that marketplace." — Jason Calacanis: Arguing against government regulation of delivery fees. "I don't want to micromanage people. I just want to be able to tell Presh and the team, I need 250 people at Angel University... I don't need to tell Prush how to do it." — Jason Calacanis: On trust but verify approach to remote management.
Implications: Founders should prioritize personalized hiring, build intentional remote culture, and test pricing early. Investors will increasingly value results over physical presence. Market timing matters, but persistence and community focus drive long-term success.
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.