Raising a seed round in 2025 is no small feat. Budgets are tight, diligence is slow, and investor optimism is hard-won. But despite all that, Pineapple Academy managed to close a fresh round of funding led by a first-time lead VC and joined by HealthStream, a billion-dollar public company and strategic partner.
The team didn’t just get lucky. They adapted their positioning, cleaned up their operations, and built trust with the right people over time. It wasn’t always smooth, and it certainly wasn’t fast. But by staying honest, focused, and flexible, they got the deal done.
Pineapple Academy is a frontline training solution for high-turnover teams in healthcare and hospitality. Their short-form video content helps workers learn practical, essential skills across a wide variety of topics, from food safety to customer service. It’s the kind of product that feels obvious in retrospect: a scrappy solution to a labor problem nearly every operator faces.
Tucker Graves, Pineapple’s co-founder and CEO, shared what the team learned along the way and what other founders can take from their fundraising experience.
1. Reposition your product to match investor priorities
When fundraising slowed, Tucker got a piece of advice that reshaped Pineapple’s pitch: Stop framing it as an L&D tool and start showing it as an operational must-have. Reframing the pitch didn’t require a new product, just a new lens. But it unlocked a completely different set of conversations.
“Someone told us: ‘Don’t be in L&D right now. It gets cut first,’” said Tucker. “That was a lightbulb moment. We reframed our product as essential for operations and process improvement. It was the same solution, but suddenly we looked recession-proof.”
The shift didn’t resonate with just investors. It helped Pineapple land a strategic partner that saw them as part of its core service offering.
2. Build relationships before you’re ready to raise
Pineapple’s lead investor in their funding round didn’t come from a cold pitch. It was someone Tucker had met early—long before the round formally opened. What made the difference wasn’t one meeting, but what happened after: consistent, structured follow-up that mirrored how Pineapple runs its own sales process.
He built a lightweight CRM for fundraising, tracked touchpoints, and treated each investor like a long-cycle deal. That approach paid off: One of those early conversations turned into the lead check when the timing was right.
Tucker is looking ahead to their next round. “We’re already starting pre-Series A conversations,” Tucker said. “We’re not asking for money. We’re just getting on the radar. We’ll send milestone updates throughout the year. If we wait until we need the money, it’s too late.”
3. Ask for help. Not just capital.
Before this most recent round, Pineapple was low on runway. But rather than try to downplay it, Tucker laid the situation bare to current investors. That move—honest, unvarnished, and a little uncomfortable—turned out to be the catalyst for getting back on track.
“I went to Dave [Lambert, of Right Side Capital] and said: our numbers are messy, our accounting firm doesn’t get SaaS, and I need help. Not more money. Just help.”
That openness paid off. It led to better advisors, better systems, and a much clearer understanding of what the business actually needed to raise.
But it also signaled something deeper: a founder who was coachable, self-aware, and committed to getting it right. As Tucker put it, “Vulnerability isn’t weakness. It’s strength. The people who’ve already invested in you are your best advisors. Let them in.”
4. Focus your business.
Pineapple Academy didn’t scale by doing more—they grew by doing less, better. Tucker and his team stopped chasing every revenue opportunity and started making deliberate tradeoffs. They dropped entire product lines that didn’t align with their core customer. They reworked pricing, narrowed their ICP to two verticals, and invested in brand strategy to clarify exactly what they do.
“We spent $40,000 on branding to get to one sentence: We’re a frontline training solution for healthcare and hospitality,” Tucker said. “Every decision flows from that.”
The company also adopted OKRs and now runs weekly reviews to keep every team accountable to three core priorities. That clarity didn’t just make operations tighter. It made the company more fundable. “We chased revenue for too long,” he admitted. “Now we’re saying no.”
Tucker's parting advice for founders who are fundraising
What stands out about Tucker isn’t just that he managed to fundraise. It’s how he did it. He was transparent with his numbers. He was clear about what needed fixing. And when it came time to pitch, he relied on focus, relationships, and momentum.
His advice to other founders? Don’t wait until you need the money. Start early. Stay flexible. Ask for help long before you ask for capital. Most of all, understand the market you’re raising into. Instead of trying to convince investors to believe in you, learn what they already believe and show them how you fit.
Fundraising is never the whole story. But when it’s done well, it signals something deeper: a team aligned, a product gaining traction, and a founder who knows how to adapt without losing direction.
Pineapple Academy is growing fast. But they’re not rushing. They’re building the kind of company that doesn’t just weather hard times. It uses them to get sharper.
