What if your first check came from someone who actually understood your scrappy MVP, your emerging market, and your ramen-burn rate lifestyle?

Ali Jamal, global operator turned full-time investor, is the founding partner of First Check Ventures—one of AngelList’s most prolific syndicates, now evolved into a pre-seed fund backing founders in 30+ countries. With experience scaling at Zynga, Agoda, and Rappi, and over 200 startup investments under his belt, Ali brings an eye for overlooked gems and the discipline of a portfolio built one $1K check at a time.

In this episode, we unpack how he bootstrapped his way from Asia to Latin America to Puerto Rico, why he doubled down on high-volume, high-conviction investing, and how First Check Ventures is winning deals by being really early—and actually helpful.

💡 Key themes we cover:

🔹 The evolution from angel to syndicate to institutional fund

🔹 How emerging market founders get more done with less—and why that matters

🔹 Tactical lessons from doing 200+ deals across multiple geographies

🔹 What syndicate leads don’t tell you about raising a fund

🔹 How to earn trust at the earliest stage (before there’s even a product)

From saving money on street food in Bangkok to outpacing billion-dollar funds with $50K checks, Ali’s story shows that being first isn't about speed—it’s about seeing value before everyone else does.

Chapters:

Welcome & Guest Introduction (00:00 – 00:38)

Ali’s Accidental Entry into VC (00:39 – 02:28)

Living Abroad & Saving to Invest (02:29 – 04:33)

AngelList & Early SPV Experience (04:34 – 07:21)

Realizing Dealflow Alpha Before the Crowd (07:22 – 08:55)

Launching First Check Ventures (08:56 – 11:09)

Going from Casual to Consistent Investing (11:10 – 14:37)

The AngelList Syndicate Explosion (14:38 – 17:32)

Becoming a Recognizable Investor Persona (17:33 – 20:48)

Why Puerto Rico? (20:49 – 22:59)

From SPVs to Fund Strategy (23:00 – 27:43)

Challenges with Syndicates & LP Dynamics (27:44 – 30:54)

Sticking to the “First Check” Thesis (30:55 – 33:22)

Investing Before Incorporation (33:23 – 35:24)

Why Capital Efficiency Matters (35:25 – 38:08)

Founder Assessments at the Earliest Stage (38:09 – 41:13)

The VC Lab Transition & Growing Up as an Investor (41:14 – 44:20)

What Syndicates Don’t Prepare You For (44:21 – 47:02)

Ali’s Fundraising Philosophy & Lessons (47:03 – 49:38)

Ali’s Portfolio Construction Strategy (49:39 – 52:22)

Borrowing from YC’s Playbook (52:23 – 54:49)

Avoiding Hype & Chasing Signal (54:50 – 57:30)

Red Flags from Founders (57:31 – 01:00:13)

How Founders Can Protect Their Early Backers (01:00:14 – 01:03:01)

When Investors Screw Over Founders (01:03:02 – 01:05:48)

Lessons from Being an LP & Angel (01:05:49 – 01:08:20)

Closing Thoughts & Where to Find Ali (01:08:21 – 01:12:20)

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