For the first time on Substack, I hosted an AMA with the Fireside PM subscribers in the subs chat. It was a great way to get a pulse on what’s top of mind for product leaders, founders, and folks just starting their journeys. Here are a few of the highlights from the latest conversation.
Onboarding as a New Hire
Q: How should a new hire prioritize their time to maximize success early on?
That’s a tough one. Ultimately, the challenge of a new hire is to earn trust, understand the customer, business, and product, and land wins. The hard part is figuring out which levers to pull and by how much, given that you only have a finite number of hours in a day.
One tactic I recommend: explicitly run your approach by your manager and ask if they think you’re spending time on the things that will maximize your onboarding success. It shows alignment and helps you avoid over-investing in the wrong areas.
Convincing Leadership to Prioritize Bold Bets
Q: What’s the most effective way to get leadership to support bold, long-term product bets?
In my experience, the formula is a vision for a step-change opportunity, data that shows the opportunity exists, and a simple plan to quickly and cheaply experiment. Leaders are more willing to back big swings if they see both the upside and a path to de-risking the bet with early experiments.
Comedy, Poker, and Thinking Skills
Q: Does trying standup comedy help with product thinking?
I don’t know if comedy sharpens product thinking directly, but it definitely makes public speaking feel 10X easier. If you can survive doing a five-minute set in front of strangers, presenting to an exec team will feel like a breeze.
For honing judgment and thinking skills, I personally like playing poker and doing some investing. Both give you rapid feedback loops and force you to confront your biases. Another exercise: make lots of small MVPs and subject them to friends and family. It’s a lightweight way to test ideas and train your instincts.
When to Raise Money as a Founder
Q: Should you raise money before product-market fit or your first paying customers?
If you can cover your burn rate with bootstrapped money, that’s the preferred way. You’ll be able to raise on better terms later, and you’ll have the freedom to pivot and experiment without investor pressure.
Once you raise, founders often feel like they’re on a shot clock to deliver good news every quarter, which can distort judgment. When I was a younger founder, I saw funding as a source of validation or pedigree. But in reality, it’s just a lagging indicator. Focus first on building something that people want to pay for.
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Closing Thoughts
What I love about these AMAs is the range of questions—from tactical onboarding advice, to pitching bold bets, to reflections on comedy and poker, to founder fundraising strategy. It reminds me that product leadership isn’t just about frameworks and processes. It’s about judgment, communication, and learning to play the long game.
If you want to be part of the next AMA, make sure you’re subscribed to this Substack (it’s free) or hit me up for private 1:1 coaching or product consulting for your company.