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SuperAngel #184: Charley Ma, first angel check investor attracting follow-ons from giants like A16Z, Coatue, First Round, Index, & Sequoia

SuperAngel #184: Charley Ma, first angel check investor attracting follow-ons from giants like A16Z, Coatue, First Round, Index, & Sequoia

Today, we're happy to welcome you to the second episode diving deep on the story of a Super Angel on! Say hi to Charley Ma, the man responsible for building and scaling multiple enterprise software startups and leading their marketing, sales, and customer success teams from $0 to $200m dollars as the first revenue hire for companies such as Plaid, Ramp, and Alloy.

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Charley's career as an operator is only matched by his career as an angel having been an early investor in breakout companies such as Stytch, Unit, Codat, Moov, Finch, and many more which have gone to raise from giants like A16Z, Bain, Benchmark, Coatue, First Round Capital, Founder’s Fund, Index and Sequoia.

Charley’s Journey Into Angel Investing 👼

🎓 Fresh out of college, Charley found himself at JP Morgan.

But this wasn't your typical finance role. No, Charley joined a research and development team focused on emerging technologies in the payments space. The curious 21-year-old analyst became fascinated by the world of payments and its endless possibilities.

As Charley delved deeper into the world of startups, he found himself engaging with fellow investors and angels. Conversations revolved around uncovering the best-performing companies in their portfolios, and Charley had a lightbulb moment. 💡

Charley’s Investment Thesis & Strategy 🎯

💡 Charley's approach was unconventional but driven by a profound understanding. He realized that time was the most valuable asset in his professional life.

As he spent most of his waking hours at work, he understood that choosing the right early-stage companies could profoundly impact his income and career prospects.

$10,000 per angel investment.

Armed with $100,000, Charley divided the amount into 10 equal parts.

He adopted a consistent check size approach, regardless of the level of excitement for each opportunity. This approach ensured that he treated every investment with the same level of consideration and avoided overemphasizing initial enthusiasm.

You have no clue which one's going to work out.

Oftentimes, the angel investment that you're right, marginally yes, could oftentimes be just the most successful angel investment versus the one that you are extremely excited about.

You shouldn't vary the cheque size based off the level of excitement.

Charley’s Core Learnings from Angel Investing 🧑‍🏫

🔫 The Quickfire Round 🔫

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