Tag: Angel Investing
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Do you have a list of customers or prospects you want to monitor news for? Here’s how to build an easy automation with Grok Projects… For me, my founders are my customers. And since I’ve got 42 investments now, it’s hard to keep track of what’s going on with all…
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I want to meet as many awesome founders as I can. So I’m automating the busywork. Here are the automations I’ve got running my investment business… Summarizing Decks I built a great little tool in Grok Projects to summarize decks in the exact format I like: Instead of paging through…
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+ AI, Angel Investing, Artificial Intelligence, ChatGPT, Entrepreneur, Finance, Grok, Investing, Silicon Valley, Startups, Technology, VC, Venture Capital, Writing+
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An amazing founder DM’ed me last week. I knew this deal wouldn’t last. Here’s the exact timeline — from cold X message to wire transfer in just five days… Tracking a Recent Investment, Minute by Minute Tuesday, June 23: 1:42pm: Cold X message received 4:49pm: I reply and ask for…
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+ Angel, Angel Investing, Business, Entrepreneurship, Finance, Founders, Fundraising, Investing, Silicon Valley, Startup, Startups, Tech, VC, Venture Capital+
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We all love to whine about YC valuations. But lately, YC has quietly become one of the best deals for investors… Getting More for Your Money When I was meeting YC companies 2-3 years ago, this is what the best ones looked like: Here’s what I’m seeing now in the…
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+ Business+ Angel Investing, Business, Finance, Founders, Fundraising, Investing, Personal finance, San Francisco, SF, Silicon Valley, Startups, Tech, Venture Capital, Y Combinator, YC+
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I just missed out on $157,000. Last year, I passed on a startup that is now raising at 25x the valuation. Here’s how I blew this deal, and what I’ll be doing differently next time… Why I Passed We’ll call this startup Supercorp. In April 2025, I had an opportunity…
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+ Angel, Angel Investing, Business, Entrepreneur, Entrepreneurship, Finance, Founders, Investing, Personal finance, Startups, Stocks, VC, Venture Capital+
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Every investor is throwing money at AI. But if you’re building in an unsexy area, is raising money even possible? A frustrated consumer hardware founder recently posed this question to Reddit. He’s seeing VC’s rip huge checks into AI while he’s struggling to raise any money at all. But there’s…
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+ Angel Investing, Angel Investor, Business, Consumer, Engineering, Entrepreneur, Entrepreneurship, Finance, Founders, Hardware, Investing, Silicon Valley, Startups, Tech, Technology, Venture Capital+
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How do angels avoid incinerating money? How do you meet the best founders? Jason Calacanis digs into that and more in his book Angel. This is the book that got me into angel investing. Nearly five years and 38 investments later, I decided it was time for a reread. This…
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+ Angel, Angel Investing, Business, Entrepreneurship, Finance, Investing, Reading, Silicon Valley, Startups, Tech, VC, Venture Capital+
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An investor passes on your startup. You can change their mind, right? Wrong. Here’s why trying to change investors’ minds is a waste of time… Minds Don’t Change Investors are interested right away or not at all. When they pass, the chance of you ever getting a dime is minimal.…
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+ Angel Investing, Business, Entrepreneur, Entrepreneurship, Finance, Founders, Investing, Silicon Valley, Startups, Tech, VC, Venture Capital+
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Here’s how a typical angel investor loses $250,000: This is what happens for most angels. They only invest in one company. The founders are not technical, and the product never launches. Their money goes up in smoke. Here’s how we can do better… Focus on Launched Products I never invest…
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+ Angel, Angel Investing, Angel Investor, Business, Entrepreneurship, Finance, Investing, Silicon Valley, Startups, VC, Venture Capital+
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I’m seeing tons of seed rounds at $40 million and up. Here’s why those will turn out to be bad investments…. Venture Funds Need Massive Growth Startups raising seed rounds at $40M need to hit $1B ARR within 10 years. That is a near-impossible task. But any less, and it’s…
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+ Angel Investing, Business, Entrepreneurship, Finance, Investing, Money, Silicon Valley, Startups, Tech, VC, Venture Capital+
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Tremendous 