You’re reading The Messy Middle: weekly deep dives on building a business, storytelling, culture, and the hard decisions behind what to pause, prioritize, and pursue.
💸 Maybe It’s Not Your Pitch Deck
Last week, I was in Riyadh speaking on a panel at the Women Shaping Wealth Summit about who gets to design the innovation economy. Somewhere in the middle of our conversation about what investors actually pay attention to, both investors on my panel said some version of the same thing: the founder's pitch deck doesn't matter.
If you've spent any time in startup spaces, you know how much time and energy founders put into their decks. In fact, there are even entire businesses built around helping you make them better.
Founders will spend weeks rewriting the market slide, rearranging the traction slide, figuring out whether their founder story belongs at the beginning or the end, and trying to make ten slides communicate the enormous thing they've been carrying around in their head for the last three years. So naturally, I asked the question I imagine a lot of founders would ask: if it's not the pitch deck, how does a founder actually stand out?
One of the investors on my panel, Emon Shakoor, CEO & Founder of Blossom Accelerator, gave an answer that completely reframed the question for me. She said that the founders she gets most excited about investing in are getting such incredible results that she's trying to figure out how to get onto their cap table.
👀 Maybe We Have This Backwards
Emon’s answer reverses so much of the way we talk about fundraising. Usually, the founder is trying to get the introduction, land the meeting, perfect the pitch, and convince someone on the other side of the table that what they’re building deserves their money. She was describing the opposite: build something compelling enough that the investor is trying to get your attention.
And there was another part of the conversation that made this click for me. Both investors basically said that with tools like AI and Claude, there’s very little excuse for having a bad pitch deck anymore. You can get help organizing your thinking, pressure-testing the story, tightening the language, and making the whole thing look pretty good without spending weeks doing it. A solid deck is increasingly just the standard, which means having a good one doesn’t necessarily make you stand out.
Of course, founders still need pitch decks. Investors need to understand what you’re building, where you’re going, and why they should care. And fundraising is ultimately about relationships: you’re asking someone to put their money behind you and your business, often for years to come. But Emon’s answer made me curious about something else: how does an investor distinguish between a business that’s having a good moment and one that’s building something with real staying power?
I imagine some of that becomes apparent in the questions that come after the pitch. Why are customers choosing this product when they have other options? What have you learned about your market that you didn’t know six months ago? When something hasn’t worked, what did you do about it? And perhaps most importantly, what makes you believe the results you’re getting today are something you can build on tomorrow?
Those questions also reveal something about the founder. How do they interpret their own numbers? Can they explain why something worked, or are they just excited that it did? Are they able to acknowledge what they haven’t figured out yet? I think there’s a lot you can learn about someone’s judgment from the way they talk about the decisions they’ve made, especially the ones that didn’t work out.
🧠 What the Numbers Can’t Tell You
Before I became a founder, I spent years working in finance, evaluating businesses and making investment decisions. I remember how much time we spent trying to understand the assumptions behind a financial model, because even the most detailed projections were ultimately based on someone’s beliefs about what was going to happen next.
Then I became a founder and found myself on the other side of those assumptions. Suddenly, I was the person making decisions about how much inventory to order, where to spend money, which opportunities to pursue, and how much risk I could afford to take, often without nearly as much information as I wanted.
I think about that experience differently now. It’s easy to admire a founder’s results once you know how things turned out. It’s much harder to evaluate the decisions they made when the outcome was still uncertain. And I keep coming back to the same question: how much of what makes a founder worth investing in comes down to how they make decisions when they don't have all the answers?
A little Riyadh red carpet moment before moderating my panel at the Women Shaping Wealth Summit 💛
🥨 Snacks
🕊️ In Bisan’s Words: Palestinian journalist Bisan Owda reflects on what it means to be denied even the basic human right to grieve. Listen to her full post here.
