Steven Plappert doesn't mince words. When the CEO of Louisville fintech Forecastr talks about his company's latest funding round—a $7 million Series A—he calls it "the most challenging fundraise to date." Coming from a founder who's navigated the venture gauntlet since 2018, that's saying something.
The round, which reportedly closed in May, drew backing from 27 investors, 18 of them returning for another bet on the financial planning software startup. Leading the charge: the Discover Financial Health Improvement Fund, a $36 million mission-driven vehicle launched by Discover in 2023. The fund targets companies building tools to shore up financial outcomes for small businesses and consumers who fall somewhere between struggling and comfortable—a lane Forecastr appears to fit neatly into.
But Plappert's candor about the difficulty raises questions. What made this round so hard? He hasn't elaborated publicly, though the answer likely lies somewhere in the broader chill that's settled over early-stage venture capital. B2B fintech infrastructure—particularly the kind that doesn't involve buzzwords like "generative AI" or "crypto"—has lost some of its shine. Investors who once moved quickly on SaaS plays are now conducting longer diligence cycles, asking harder questions about unit economics, and cherry-picking only the most defensible business models.
Still, Forecastr managed to pull together a sizable syndicate. That 18 of the 27 backers came back for more suggests existing investors saw enough momentum to overcome their hesitation. Valuation? Undisclosed, naturally.
What Forecastr Actually Does
The company sells financial planning and analysis software tailored to startups—think scenario modeling, cash runway tracking, and hiring plan forecasting, all tied together with integrations into QuickBooks Online and Xero. But Forecastr doesn't stop at software. It pairs its platform with hands-on analyst support and fractional CFO services, positioning itself as "software plus expertise." The pitch: founders who need more than a spreadsheet template but can't yet justify a full-time finance chief.
It's a crowded space. Jirav, Finmark (parts of which have been acquired or are winding down), and Cube all play in similar territory. Upmarket, heavyweights like Planful and Anaplan loom. In April, Planful rolled out an AI-powered planning assistant, a reminder that even established players are scrambling to layer generative capabilities into their workflows. Forecastr will need to move fast to keep pace.
The company now serves roughly 550 customers, up from around 400 a year prior, according to local press accounts aggregated by Dealroom. Not explosive growth, but steady—perhaps more than the founders expected given the broader startup slowdown.
The Mission-Driven Lead
The Discover Financial Health Improvement Fund isn't your typical venture outfit. Managed by ResilienceVC and Chartline Capital, with evaluation support from the Financial Health Network, it focuses explicitly on improving financial outcomes for underserved segments: small businesses and lower- to middle-income consumers. Forecastr joins a portfolio of roughly 10 active investments. (As of late May, the fund's public portfolio page hadn't yet updated to reflect the new deal, though law firm Reitler Kailas & Rosenblatt confirmed it represented DFHIF in the Series A Preferred Stock transaction.)
For Forecastr, the alignment makes sense. Its customers skew heavily toward early-stage founders navigating the treacherous waters between seed and Series A—precisely the kind of financial vulnerability a mission-driven fund might care about. The company's own content strategy leans into this moment: recent blog posts from April and May walk founders through Series A expectations, fundraising prep, and financial modeling best practices. It's marketing, sure, but it also signals where Forecastr sees its value proposition resonating most.
The Team and the Timeline
Plappert co-founded the company in 2018 alongside Logan Burchett (now COO), Jonathan Frazier (Chief Data Officer), and Steven Ambs. The team went through Techstars Anywhere in 2020, emerging with early traction and a playbook for remote-first growth. LinkedIn pegs the current headcount at 60 employees, though the company's official band remains 11–50—a discrepancy that's common as startups update profiles at different speeds.
Forecastr has also started pushing beyond U.S. borders. In January, it inked a partnership with Standard Ledger, an Australia-based firm, to bring its modeling and CFO services to founders across the Asia-Pacific region. Whether that international push will meaningfully move the needle or remain a niche play is yet to be seen.
What's Next—and What's at Stake
Forecastr hasn't detailed how it plans to spend the $7 million. The typical playbook would call for headcount expansion, product development, and customer acquisition. But given Plappert's comments about the difficulty of the raise, capital efficiency likely sits high on the priority list. Burn slower, prove more—that's the mantra for startups navigating today's market.
The round is a meaningful milestone for a Louisville-based company operating in a category dominated by better-funded, often West Coast-based competitors. Whether $7 million proves sufficient to outpace them will hinge on execution, and perhaps on whether the broader venture market thaws in the months ahead. For now, Forecastr has bought itself time. What it does with that runway will determine if Plappert's next fundraise is any easier—or if he'll be using the same words again.
