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This Week in Startups

Jason’s ultimate dream mega-purchase + Founder Q’s | E2228

45 min episode · 2 min read

Episode

45 min

Read time

2 min

Topics

Productivity, Investing, Startups

AI-Generated Summary

Key Takeaways

  • Customer validation framework: Secure two to three customers before scaling to validate the problem exists broadly, not just for one uniquely dysfunctional client. Single customer validation risks building bespoke software for an isolated edge case rather than a scalable market opportunity.
  • VC outreach protocol: When investors reach out unsolicited, research their portfolio, log them in a CRM, and delay meetings until fundraising begins. Control the conversation by setting meeting times months ahead on your terms at your office, maintaining leverage as the scarce resource.
  • Investor quality assessment: Conduct backdoor references by calling portfolio company CEOs directly to evaluate investor value-add before accepting capital. Seventy percent of investors add no value or detract value, making due diligence on investors as critical as their diligence on founders.
  • Geographic investor selection: European VCs investing in US-focused startups can provide advantages if founders leverage their European heritage for deal flow priority. Quality investors and deals transcend geography, so evaluate based on terms, reputation, and support rather than location alone.

What It Covers

Jason Calacanis addresses founder questions on validating customer problems, handling VC outreach, taking European investor money for US startups, and discusses extravagant purchases he avoids despite financial success.

Key Questions Answered

  • Customer validation framework: Secure two to three customers before scaling to validate the problem exists broadly, not just for one uniquely dysfunctional client. Single customer validation risks building bespoke software for an isolated edge case rather than a scalable market opportunity.
  • VC outreach protocol: When investors reach out unsolicited, research their portfolio, log them in a CRM, and delay meetings until fundraising begins. Control the conversation by setting meeting times months ahead on your terms at your office, maintaining leverage as the scarce resource.
  • Investor quality assessment: Conduct backdoor references by calling portfolio company CEOs directly to evaluate investor value-add before accepting capital. Seventy percent of investors add no value or detract value, making due diligence on investors as critical as their diligence on founders.
  • Geographic investor selection: European VCs investing in US-focused startups can provide advantages if founders leverage their European heritage for deal flow priority. Quality investors and deals transcend geography, so evaluate based on terms, reputation, and support rather than location alone.

Notable Moment

Calacanis reveals private aviation remains his most coveted but unjustifiable expense, with round trips costing fifty to one hundred thousand dollars. He debates whether cognitive load from additional assets outweighs their benefits, preferring to invest capital in Founder University companies instead.

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Episode Transcript

Now that you're doing so well financially, what is a purchase that you'd like to make but can't bring yourself to do so because it feels too extravagant? Answer this honestly. Tell the people what you, even Jason Calacanis, will not break out the checkbook for. It's definitely private aviation. I've been trying to hold off on doing this for a long time. The great unjustifiable expense of spending, you know, $50,000 going somewhere or a 100,000 on a round trip, that seemed absurd to spend that. The other one, I would say, that I sometimes sweat is buying a really expensive sports car. I love Corvettes, and I really wanna buy a barn dominion, which is like a big open fancy barn that's kinda like a man cave, but Texas style. Do I buy this ZRX one for $250,000, or do I buy five $50,000 Corvettes and have a little collection? A lot of these things become cognitive load. This week in startups is brought to you by lemon.io. Building a great team is essential to any business. Lemon is a marketplace of vetted, experienced engineers ready to take your company to the next level. Get 15% off your first four weeks of developer time at lemon.io/twist. Vanta. Compliance and security shouldn't be a deal breaker for start ups to win new business. Vanta makes it easy for companies to get SOC two reports fast. Get $1,000 off for a limited time at vanta.com/twist. Northwest registered agent. Starting your business should be simple. With Northwest registered agent, you can form your entire business identity in just 10 clicks and ten minutes. From LLCs to trademarks, domains to custom websites, they've got you covered. Get more privacy, more options, and more done. Visit northwestregisteredagent.com/twist today. Today's founder question, Jason, comes from our dear friends over at the r/startups subreddit, and I found a question that I had absolutely never seen before. So I thought it was the perfect thing to bring to us today. From our our dear friend Entire Chest, quote, I signed a $20,000 paid pilot, but it's a shark bite problem. Interesting framing. Shark bites are big crises because you're bleeding versus mosquito bite, just kind of irritation. They found a big problem to solve. What they did was they found that there's trucking companies that transport fluids, and often they get the wrong fluid in the wrong truck or the wrong truck goes to the wrong destination. And so they made a product to fix this, and they signed a $20,000 pilot. They found a problem in the market. They made a solution for it. And then they went out and did more market research and discovered that other people in the fluid trucking industry don't have this problem. They seem to have found a uniquely messed up first customer. And so I was just really curious, how common is it to accidentally index on the wrong customer and drive in the wrong way? This is …

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