Episode Summary
Executive Summary: Roy from Bloomberg Beta argues that fundraising is driven less by deck polish and more by trust, introductions, and a clear reason a company can be an outlier. He explains how VC incentives, fund size, and valuation shape outcomes, defends secondary for founders in the right situations, and emphasizes that automation and future-of-work disruption are already happening now, not someday.
Main Topics: How VCs actually decide to invest (Priority: 5/5): Roy reframes fundraising as a filter for whether a partner will continue doing work, not a pure evaluation of business quality. He says the first signal is who introduced the founder and whether the VC can explain the company internally. Why a company is an outlier (Priority: 5/5): He argues investors need a fact-based reason to believe a startup could be extraordinary—something like first, best, or only—rather than generic traction claims or deck storytelling. Bias, access, and diverse sourcing (Priority: 4/5): Roy acknowledges intro-based fundraising creates bias and says Bloomberg Beta tries to counteract it by using data to find likely founders before they raise, which surfaced a more diverse founder pool. Fund economics, valuation, and ownership (Priority: 5/5): He explains that valuation is often a function of fund strategy and desired ownership, not an abstract market price, and that larger funds can pay more because they need different economics. Founder secondary and personal finance (Priority: 4/5): Roy advocates thoughtful secondary at later stages to reduce founder stress, arguing that founder well-being can improve company performance, but timing and dosage matter. Automation and the future of work (Priority: 5/5): He says automation is already reshaping jobs today, that no occupation is fully safe, and that the practical answer is to keep learning and build entrepreneurial skills. Founder mentality and rejection (Priority: 4/5): Roy advises founders to treat VC rejection as feedback on fit, not truth about the business, and to use the process to quickly disqualify the wrong investors.
Key Arguments: Warm intros matter because the introducer’s identity carries information and helps a VC justify a deal to partners. A pitch must answer two questions: why this company can be an outlier, and why this VC is the right investor. Cold emails fail often because they rarely show enough customization or a compelling reason the recipient should be excited. VCs are constrained by internal politics and career incentives, not just investment judgment, which shapes behavior. Valuation is often driven by fund size and target ownership; bigger funds can pay more, smaller funds are price-sensitive. Secondary can be healthy when founders have enough proof and personal financial stress is distracting them from building. Automation is not a distant threat; it is already reducing jobs, suppressing wage growth, and changing operating models. Founders should reference-check funds and should also use investor interactions to quickly determine if there is a fit. Bloomberg Beta tries to reduce intro bias by using data to identify likely future founders before they start companies. Entrepreneurship is increasingly a core life skill and may be the best hedge against labor-market instability.
Data Points: Bloomberg Beta fund size: $75 million - Mentioned while introducing Roy and Bloomberg Beta, with a caveat about LinkedIn accuracy. Company review volume: Tens of companies per month - Roy said the fund meets with tens of companies monthly, not 100. Personal new-company meetings: About 3 companies per week - Roy estimated his own pace of new meetings. Real cold outreach success rate: Once every 3 to 4 months - He said a cold email has to be unusually well done to get real traction. Daily inbound signal introductions: 3 to 5 per day - Roy estimated the number of non-noise introductions he gets daily. Founder prediction diversity result: Twice the proportion of female founders - Bloomberg Beta’s data-driven founder prediction exercise produced a more diverse predicted group. Startup outcome example: $2.8 million first day on Kickstarter - Roy cited his own company’s Kickstarter launch as a turning point after prior VC pass-backs. A-round example: $8.5 million Kickstarter campaign - He referenced this amount when explaining why one VC later admitted passing was a mistake. Portfolio fundraising example: $20 million A round - Roy mentioned this as the A round raised by the company he co-founded. Time to judge interest: Under an hour to over two days - He gave speed-of-response as a heuristic: under an hour means strong interest; over two days usually means no. Founder background example: 8 and 10 years old - Roy referenced his kids’ ages when discussing how he thinks about preparing them for the future of work. Employment metric: A hire every eight seconds on LinkedIn - Used in a sponsor read to illustrate LinkedIn’s hiring volume.
Pivotal Quotes: "the vast majority of the fight is already won or lost" — Roy: He described how much information a VC infers from the first email and introducer. "Why should I believe this is an outlier? ... Why me?" — Roy: He summarized the two core questions professional investors ask when evaluating a startup. "Your job is to disqualify leads" — Roy: He reframed fundraising as an enterprise-sales process where founders should quickly filter out bad-fit investors.
Implications: Founders should optimize for trust, fit, and a crisp outlier narrative—not just polished decks. Investors may need better sourcing to reduce bias. AI and automation are already reshaping work, making adaptability and entrepreneurship more valuable.
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.