STARTUP or SHUTUP! : Startup Playbook for Founders & Creators · Colin Fraley | Founder & Startup Playbook Coach

How to Become an Investor | Andrew Ackerman

·1 hr 59 min·5 clips

Andrew calls TAM-SAM-SOM useless and says two of the three numbers are probably wrong.

The host opens by framing Andrew Ackerman as someone who has sat on both sides of the table. Andrew starts with his birth in Tel Aviv while his dad was studying medicine in Israel. He says that experience helped pull his family back to the States. He also says entrepreneurship skips a generation in his family, even though both grandparents were entrepreneurial in different ways. One grandfather owned candy shops and moved them from rougher neighborhoods to better ones as the areas improved. Andrew laughs through the memory and keeps the tone light. The host keeps asking straightforward, founder-focused questions. Andrew answers plainly in a way that fits the show’s conversational style. The episode spends time on how founders and investors should think about signals. Andrew argues that a startup needs a convincing “why now.” He says that when you narrow thousands of companies down to a smaller interview list, recent timing matters a lot. He also pushes back on buzzword-heavy pitches. The conversation turns to agentic AI and the flood of startups claiming that label. Andrew calls out how often new technology gets layered on top of old ideas. He jokes that many founders cannot clearly define what they are saying they build. The host and Andrew trade examples from a conference full of AI pitches. Andrew treats the category as partly real and partly startup fairy dust. The back half leans into practical advice for founders. He tells them not to cold email him directly. He says they should contact one of his portfolio companies instead. He also returns to the value of empathy. The show keeps its friendly rhythm and never gets overly formal or academic. That tone makes the advice easier to hear. The episode ends with Andrew sharing where listeners can find him and his book.

As heard by us

A grounded founder-to-investor conversation with useful filters and little gloss.

Andrew Ackerman's conversation reads as a practical guide to how an early-stage investor weighs founders and ideas. His experience as both founder and investor gives the discussion weight, especially when he explains why timing matters, how cold email can work, and how to tell…

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Why you'd press play

You want investor advice that sounds like a founder who has been on both sides of the table.

Read the full recommendation in PlayNext →

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