Fifteen years ago, a renowned venture capitalist made what turned out to be a billion-dollar oversight by passing on Airbnb. Here's how it unfolded and what we can learn from it. Back in 2009, Airbnb had just earned a spot in Y Combinator (YC), but the startup was facing an uphill battle. Their growth was sluggish, and finding investors who believed in their vision was proving to be difficult. Enter Paul Graham, co-founder of YC, who saw something special in Airbnb. He was convinced of their potential and decided to introduce them to Fred Wilson at Union Square Ventures, an investor known for backing successful companies like Twitter, Tumblr, and Etsy. But when the pitch landed on Fred's desk, he passed. Why turn down Airbnb? The idea just didn’t resonate. Fred later explained: “We couldn’t wrap our heads around air mattresses on living room floors as the next hotel room.” The concept seemed too unconventional and didn’t fit into the established mold of the hospitality industry. Years later, Fred reflected on that decision: “We made the classic mistake that all investors make. We focused too much on what they were doing at the time and not enough on what they could do, would do, and did do.” Today, Airbnb is a household name with a valuation soaring to $73 billion, revolutionizing the way we think about travel and accommodations. What seemed like a quirky idea of renting out air mattresses has grown into a global business offering unique lodging experiences in almost every corner of the world. The takeaway from this story is a powerful reminder for investors and entrepreneurs alike: Early-stage investing isn’t just about the idea—it’s about betting on people, their vision, and the possibilities of what they can achieve. Sometimes, the greatest opportunities lie beyond the limitations of what we can see right now. Would you have taken the leap on Airbnb back then, or would you have missed out too?

You’ve pitched again and again, but there’s still no traction. It’s exhausting—and it feels like you’re missing something. Jason Fried, the co-founder of Basecamp, was in the same place. After endless pitches without results, he decided to stop selling features and start selling the problem his product solved. That simple shift made investors pay attention. Maybe it’s not your idea—it’s just how you’re pitching it. Let's refine your pitch and finally get the results you deserve. Zero to Millions Club: How many pitches have you done with no luck? Let’s talk about what might be missing. #PitchBurnout #FounderPain #ZeroToMillions

What's been the biggest challenge for you when trying to turn an idea into a reality? Are you stuck on something? Whether you’re starting out or growing your SaaS idea, we’re here to help! Drop your questions below, and we’ll make sure to guide you through every step. ✨ How to Submit Your Questions: 1. Think about your biggest challenge: Is it strategy, tech, growth, or something else? No question is too small! 2. Write your question clearly so we can give the best possible advice. 3. Can’t make it to the live session? No worries! Just let us know, and we’ll cover your question during the meeting. You’ll get a recording with the answers. 4. We’ll follow up with you directly each week to ensure you’re moving forward and staying on track! and share a vid. Thanks!

In today's challenging fundraising environment, founders need to think strategically about extending their runway. With deals taking longer to close and investors being more selective, extending your runway can provide a crucial buffer to keep your company moving forward. Here's how you can effectively calculate and extend your runway, based on insights from Sequoia's guidance. What is Runway? Runway refers to the number of months your company can continue operating before running out of cash. It’s calculated by dividing your cash balance by your monthly burn rate (the amount of cash you’re spending each month). Example Calculation: - Cash balance: $10 million - Monthly burn: $500,000 - Runway = $10 million / $500,000 = 20 months However, to get a more accurate picture, Sequoia recommends considering any existing debt when calculating your cash balance: Cash balance = Cash - Debt Debt is borrowed money that eventually needs to be repaid, so factoring it in will help you better understand your true runway. How to Use the Runway Calculation Recalculating your runway every month is essential for staying on top of your company’s financial health. When your runway approaches the 12-18 month mark, it’s time to start preparing for fundraising, especially in the current market, where closing deals may take longer than expected. Knowing your runway gives you more than just a timeline; it helps set targets and align fundraising efforts with milestones that investors look for. Questions to Consider: - How often are you recalculating your runway? Monthly calculations can help you stay prepared. - Are you factoring in all potential liabilities, like debt, when assessing your cash balance? This can give a more realistic view of your financial situation. - What milestones can you realistically achieve in the next 12 months to attract investor interest? Setting goals aligned with investor expectations can make fundraising more effective. Strategies to Extend Your Runway

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