First Check Calls Game

First Check Calls Game

Most people think they’re not qualified to make investment decisions. Cheryl Kellond thinks that’s exactly the problem. A 3x founder, 3x Ironman, 4x mom, and CEO of PlayMoney, Cheryl is on a mission to open up early-stage investing to the people who actually understand the problems worth solving. In this episode, she challenges the outdated model of capital allocation and makes the case that the real barrier isn’t money, expertise, or access. It’s a system built for a world that no longer exists.

At its core, this is a conversation about decision-making as a skill. Cheryl breaks down why small checks, consistent reps, and learning by doing matter more than waiting until you’re “ready.” She and Mack get into the math behind portfolio building, the reality that losses come before wins, and why the only thing that actually predicts success is how many decisions you make. If you’ve been sitting on the sidelines, consider this your push: first check calls game.

Stuck on a Decision? Start Here.

Stuck on a Decision? Start Here.

When a decision won’t move, most teams do the same thing: gather more data, debate options, push harder.

Pam Scott and Di Tompkins take a different approach. After 25+ years of working together, they’ve learned that when something feels stuck, it’s usually not about the answer. It’s about the question. Here are a few ways they think about it:

Interrogate the question

Before jumping to solutions, slow down and unpack what’s actually being asked. Is the question framed too narrowly? Too broadly? Is it even solving the right problem?

Pam and Di will spend time pulling a question apart from every angle: what’s behind it, what’s driving it, what might be missing. Because once the question shifts, the entire conversation tends to change with it.

You can’t solve everything from the inside

There’s a reason outside perspective matters.

They describe it as bringing a different “color to paint with.” When you’re too close to a problem, you’re limited by your own context, assumptions, and history. A new perspective changes how you see the problem in the first place.

Insight should open things up

Insight isn’t there to confirm what you already think, it’s there to challenge it. The goal isn’t more data. It’s a deeper understanding that creates movement. The kind that surfaces new opportunities, reveals tension, and pushes thinking in a direction you hadn’t considered before.

Know when it’s intuition versus bias

Instinct plays a role in decision-making, but it’s not always reliable. The real skill is knowing when your intuition is grounded in experience and pattern recognition and when it’s being shaped by bias, fear, or habit. That distinction is what leads to better, more confident decisions.

People don’t need to agree, but they need to feel heard

Not everyone needs to be aligned on the final decision, but they do need to feel like their perspective was considered. When people are part of the process, decisions move faster and land more effectively. 

Getting unstuck isn’t about forcing an answer. It’s about seeing the problem differently.

You can hear how Pam Scott and Di Tompkins put this into practice in their full conversation on The Cred Podcast.

Question the Question with Pam Scott & Di Tompkins

Question the Question with Pam Scott & Di Tompkins

Feel stuck on a decision? Try interrogating the question.

Pam Scott and Di Tompkins have been solving hard problems together for decades, and their first move is almost always to question whether someone is solving the right problem. As co-founders of The Curious Company, they bring outside perspective to mission-driven leaders who’ve hit a wall: a different color to paint with, a reframed question, and the kind of honest conversation most organizations aren’t having internally.

On this episode of The Cred Podcast, Mack sits down with two genuinely curious women who listen for a living, challenge with warmth, and have built a 26-year partnership by celebrating what makes them different. It’s a conversation about creativity, decision-making, and what happens when you finally stop trying to answer the wrong question.

Lana Kerr: Lead with Conviction, Execute with Consensus

Lana Kerr: Lead with Conviction, Execute with Consensus

In this episode of The Cred Podcast, Lana Kerr joins Mack McKelvey for a candid conversation about decision-making as a founder, CEO, and leader. From trusting instinct in the early stages of growth to learning when to slow down and bring in more voices, Lana reflects on how her approach has evolved over time. She talks about the difference between making business decisions and people decisions, the importance of starting with the desired outcome, and why culture fit is just as important as credentials. The result is a thoughtful look at what it really means to lead: making the call, owning the consequences, and keeping the team moving with momentum in the same direction.

As Lana puts it, leadership is often 80% psychology and 20% strategy because a team’s mindset and energy shape outcomes just as much as the plan itself.