Practical Product Ep 4: The Curse of the 1st PM – Part 2: The PM View with 4-time 1st PM, Hostos Monegro

Why is it such a struggle for 1st PM hires to succeed? What are the challenges from the perspective of a product leader who has done this before? How can you avoid being a casualty of the 1st PM curse?

Today, we answer those questions and a lot more.

A chance meeting…

Back in 2019, I was living in New York City. I was meeting other PMs in town, and by chance was connected to Hostos Monegro. As it turns out, we had a lot in common, as we’d both been a 1st PM multiple times at startups.

As the conversation continued, we realized there was *a lot* in common between our experiences. It helped me realize that the situations I experienced were possibly less about me, and more about the nature of the job. It ultimately led to the inspiration for the now oft-discussed post, “Why you want to be the second 1st PM.”

Knowing how much credit Hostos deserved for inspiring and helping craft the ideas of that post, I knew there was no one better to talk about the product manager perspective than him. When I started planning this podcast, he was one of the first people I asked to come on the show, and this week’s episode is the product of that discussion.

The Curse of the 1st PM – Part 2 w/ Hostos Monegro, 4-time 1st PM

If you haven’t read it yet, the best place to start is reading my 2019 post, “Why you want to be the Second 1st PM” to get context on this unique role that comes with special challenges, and sometimes a lot of baggage. You can also check out Part 1, with a CEO who hired (and fired) a 1st PM recently here.

Today’s discussion with Hostos dives into lessons learned on having made the majority of his career being either the 1st PM, or as our original post called it, the *second* 1st PM (who comes after the first one didn’t work out).

If you’ve ever thought you wanted to try being a 1st PM, or already are one, this is a great episode for you. We cover key topics like how to screen for the right founders to work with, why this role can be awesome and fulfilling, and how to avoid some of the common pitfalls that come with the curse of the 1st PM.

Highlights of the episode include discussing:

  • (2:14) – What is it like being a 1st PM the 4th time around?
  • (5:53) – How did you think about filtering the Founder when looking for a 1st PM role?
  • (9:14) – What are the awesome parts of this kind of role?
  • (15:07) – What are some of the hardest lessons you’ve learned as a 1st PM?
  • (25:17) – Advice for someone interested in taking on the 1st-PM role
  • (38:40) – What should potential PM’s look for in a company to determine if it’s a good fit?
  • (46:52) – Recommendations if you think some of these 1st PM pitfalls apply to your situation
  • (48:11) – Advice for founders thinking about hiring their First-PM
  • (54:00) – How the First-PM be set up for success

You can also learn more about Hostos or get in touch with him on Linkedin and Twitter.

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One thought on “Practical Product Ep 4: The Curse of the 1st PM – Part 2: The PM View with 4-time 1st PM, Hostos Monegro

  1. Pingback: » Why You Want to be the *Second* 1st PM Building Customer Driven SaaS Products | Jason Evanish

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