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.

Want to be the first to hear about new episodes of the Practical Product podcast, and other blog posts I write about Product Management? Subscribe here:

Practical Product Ep 3: The Curse of the 1st PM – Part 1: The Company View with Pulkit Agrawal of Chameleon

Why is it such a struggle for 1st PM hires to succeed? What are the challenges from the perspective of the CEO who hires them? What do founders learn in the experience when seemingly inevitably, the 1st PM they hired with the best of intentions didn’t work out?

Pulkit Agrawal mentioned me and my post on “Why you want to be the 2nd 1st PM” when he lived this challenge firsthand:

And knowing he had just gone through this, I knew we had to talk about it on the Practical Product podcast. That’s why this week’s episode is all about it.

The Curse of the 1st PM – Part 1 w/ Pulkit Agrawal, CEO of Chameleon

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.

Today’s discussion with Pulkit helps answer the question you may have from the post, “How does this happen?” Pulkit read my blog post, new the risks, and yet it still happened.

Are all 1st PMs doomed? Probably not, but the challenges and unique factors of being an early stage startup do make for an ever-changing set of circumstances that can make someone who was the right choice when hired no longer the right person 6-18 months later.

Pulkit and I have a really candid conversation about what happened, what he learned, and most importantly what he’ll do differently with the second 1st PM (who he just hired).

Highlights of the episode include discussing:

  • (5:35) – How has your approach changed for hiring PM #2?
  • (6:27) – What got you excited about the person you ultimately hired for the #1 role?
  • (13:52) – When did you start to realize things may not be working out?
  • (18:28) – How did you handle the transition of a PM leaving the team?
  • (25:13) – Is it inevitable that the first PM will never be a perfect fit?
  • (34:02) – How are you thinking about changing your hiring process the second time around?
  • (35:44) – What advice would you give a founder who’s considering hiring their first PM?
  • (43:17) – How can the founder set the PM up for success?
  • (45:03) – What advice would you have for PM’s interviewing for a first PM role?
  • (48:52) – What are some red flags candidates need to look out for?

You can also learn more about Pulkit’s company at Chameleon.io, and check out their blog to learn more product management and user onboarding tips.

Want to hear about every episode of the Practical Product podcast as soon as it drops, and other blog posts I write about Product Management? Subscribe here: