There is a moment in every startup’s life when imagination eventually gives way to math.
I’ve heard this story hundreds of times before. Founders are rewarded for vision and lauded as dreamers. They pitch an idea, raise a Seed round, build their first product, and iterate.
As Shay Grinfeld, a General Partner at Greenfield Partners, said, companies repeat this loop “20 or 30 times” until they land on the one product when the penny drops. “‘They said ‘You know what, actually hits a nerve’,” he told me.
For this episode, I spoke to Grinfeld about being an early growth investor, and what happens when companies reach their initial targets in revenue: An achievement, of course, but also the beginning of a much harder phase.
Growing a Dream into Profit
“That’s when we meet them,” Grinfeld says. The point where early momentum must turn into durable growth, usually around Series B and C, optimism alone is no longer enough. Growth investors arrive with a different question: can this company scale its go-to-market strategy once identifying a successful product-market fit, and will it do this faster than the cost of capital?
“You have to grow at a cost that is cheaper than the cost of capital,” he told me. “Otherwise, you will not get the funding that will allow you to grow.” According to Grinfeld, what separates founders who push forward from those who sell early, he adds, is not recklessness but “bravery with confidence… and knowledge.”
Greenfield Partners was founded in 2016 and invests in early to growth stages in Infrastructure, Vertical Software, and Deep Tech. It has $1 billion in total assets under management after closing a $400 million third fund in 2025.
The “7 Pillars of Go-To-Market”
One of its strongest areas is structured thinking around go-to-market and company building. Our conversation frequently referenced the “7 Pillars of Go-To-Market”, when Grinfeld describes growth failure as a structural issue rather than one singular mistake. “Every time you fix something, something else breaks naturally,” he says. For example, hiring ahead of the pipeline creates idle sales teams, and scaling leads without customer success can erode retention.
The problem is rarely one pillar in isolation. To address this, Greenfield leans heavily into these pillars as concepts: strategy, sales operations, hiring and enablement, lead generation, partnerships, and customer success. The firm has even written playbooks available for founders to glean their insights.
The most underappreciated challenge in that phase, he argued, is the gap between product-market fit and what he calls product-market sales fit. “That’s the moment that you think you can actually sell your product at a cost that is cheaper than the cost of capital,” Grinfeld says. It shows up when non-founders can sell, when the pipeline becomes repeatable, and when revenue sees a predictable pattern.
“When it actually clicks,” he says, “it’s magic — because you can start compounding it.”
A Signal For Leadership
In the end, growth comes down to leadership. The founders who make it through the transition are not the ones with the loudest narratives, but the most adaptable mindsets. “Hungry, humble, smart — in that order,” Grinfeld says.
You can watch the entire exchange in the video above.
