We see value where venture stopped looking.
Founded by Jason Mackey and Yuri Cataldo, RavenRock was built to serve a market that no one else was serving, and to name a category that no one else had named.
Between venture capital and private equity sits an enormous, underserved gap. Thousands of venture-backed software companies with proven products, paying customers, and real revenue find themselves stranded after their last institutional round. They're growing, just not fast enough for venture's return requirements. They're generating revenue, just not enough for PE to engage. They fall through every crack in the institutional capital market.
RavenRock works with the investors who hold these companies and the founders who run them. We start with a clear read on the business. When capital is the right answer, we invest deal by deal alongside a network of co-investors and bring a hands-on operating playbook: reduce burn, deploy AI tooling, and build a path to profitability. We don't come in to take over. We come in to unlock what's already there.
A straight read on a stuck company. Free.
Every portfolio has a few companies that are too slow for the next round and too small to sell well. They take up board time, weigh on marks, and rarely get an outside look.
Send us one. After a one-hour call, you get a one-page written Read:
The real problem
A product problem or a capital structure problem, and how to tell.
The profitable version
What the company looks like at breakeven on its current revenue.
The preference stack
Who receives what at realistic exit values.
The path
Bridge and restructure, sell, or wind down in an orderly way, with our reasoning.
No fee. No obligation. No pitch attached. What you share stays confidential. If a bridge makes sense, we'll say so. If a sale or a wind-down is the better answer, we'll say that too.
Request a ReadA structured bridge, not a blank check.
When a company needs capital to reach profitability, we invest deal by deal alongside co-investors, on terms built for the situation.
Structured capital
Capital is deployed through a structured convertible note with performance-linked terms, protecting the downside while giving the company every opportunity to succeed on its own terms.
Operational conviction
We get inside the business: deploy modern AI tooling, cut burn, reduce complexity, and refocus the team on what's working. The product exists and customers are paying. Our job is to remove what stands between the company and profitability.
Performance-linked governance
Governance ratchets tie control to results. Hit the milestones and the note converts at a fair valuation, and everyone wins. Miss them and increasing rights ensure the company still reaches a sound outcome.
A defined outcome
Success is defined before a dollar is deployed: a path to profitability, a strategic sale, a PE acquisition, or durable cash generation. We don't hold forever and we don't hope for the best.
Operators, not spectators.
Jason Mackey, Managing Partner
A founder and investor who has started eleven companies since 2008, across software, energy, media, and defense. Some worked. Some didn't, so he knows a stranded company from the inside. He built an executive network of 300 operators and has spent years advising principals and family offices on negotiations that call for judgment and discretion, which is most of what restructuring a cap table requires.
Yuri Cataldo, Partner
An MIT MBA with deep experience in construction, manufacturing, and industrial AI. He co-founded Autodesk's Innovation Program, evaluating 800+ startups, and applies that pattern recognition to assessing and restructuring stranded SaaS companies.
What we look for.
We work with a small number of companies, deeply, not a spray of checks. If a company in your portfolio matches most of what's below, send it to us for a Read.
Post-revenue
A live product and customers already paying.
$2M to $5M ARR
Real revenue, below PE's radar, past venture's interest.
B2B software
SaaS and software-led businesses with durable gross margins.
Stranded between rounds
Strong product, real customers, no clear path to the next round.
A line to profitability
Unit economics that work once the cost base matches the revenue.
Founders open to a partner
Willing to take on hands-on operating work and a real governance structure.
For investors holding stranded positions, and founders running out of runway. Start here.
Request a ReadTell us about one stranded company. We'll set up a one-hour call, then send you a one-page written Read. Free and confidential.
Thanks. I'll reply by email to set up the call.
Tell us what's on your mind. We read every message.
The gap nobody else will touch.
Post-revenue software companies with proven products and paying customers get stranded after their last institutional round, too slow for venture's return math, too small for private equity to engage. RavenRock is built for that middle.
| Venture Capital | Venture Equity | Private Equity | |
|---|---|---|---|
| Stage | Pre-revenue to growth | Post-revenue, stranded | Mature, profitable |
| Thesis | Outsized winners | Unlock trapped value | Cash flow & control |
| Capital | Priced equity | Structured note | Buyout / majority |
| Role | Board seat | Hands-on operating | Control & overhaul |
| Outcome | Next round / IPO | Profitability or sale | Exit after hold period |
We call it Venture Equity.
Notes on the gap, and the companies in it.
We write about Venture Equity, operating post-revenue software businesses back to profitability, and the structural blind spot between venture capital and private equity.
Substack
Read RavenRock on Substack
X
@ravenrockvc
Straight answers for investors and founders.
A category we created for post-revenue software companies caught between their last venture round and profitability. It pairs structured capital with a PE-style operating playbook. We're not early-stage venture and we're not traditional private equity. We're built for the gap between them.
A free, confidential, one-page assessment of a single stranded portfolio company. It covers the real problem, the profitable version of the business, the preference stack, and the path we'd recommend. Investors use it to make a decision they've been putting off.
It's how we meet the companies in our category. Most Reads end with a recommendation that has nothing to do with us. Some end with a bridge. Both are worth our time.
Venture-backed software companies with proven revenue, strong gross margins, and no clear path to their next raise. The product works, the customers pay, and the team is still standing, but the capital structure no longer serves them.
They're not growing fast enough for venture's return requirements. That says nothing about whether the business works. Most venture funds need breakout winners. We work with proven businesses.
When we invest, we use a convertible note with performance-linked governance terms. If profitability milestones are met, the note converts at a fair valuation. If they're missed, governance ratchets give RavenRock increasing control. Either outcome generates value.
We move fast. Headcount is right-sized, AI tooling is deployed, and infrastructure costs are cut dramatically. Within months the company is operating leaner, serving its best customers better, and generating profit on the same or slightly reduced revenue. We'll walk you through it.
A path forward that doesn't require raising a round they can't raise. Most founders of stranded companies are trapped by their own cap table. The preference stack means they see little at a modest exit. We restructure the economics, execute a clear operational plan, and create a realistic exit that actually puts money in their pocket.
Every stranded portfolio company drags down IRR, takes a board seat, and complicates the next fundraise. We start with a free Read. If capital is the answer, we offer a clean solution: new money in, the board seat off your hands, and a realistic path to recovering value from a position you were likely writing down.
Acquirers want profitable businesses they can bolt on immediately. PE rollups want scale and cash flow. We take companies that are neither: pre-profitability, mid-restructuring, with complex governance, and do the hard operational work. They're buying finished products. We're finishing them.
Deal by deal, alongside co-investors, while we build a track record in the category we named.
NOTICE: The information on this website is provided for general informational purposes only and does not constitute an offer to sell or a solicitation of an offer to purchase any securities. Any securities offered by RavenRock will be offered only to accredited investors pursuant to Rule 506(c) of Regulation D and only through definitive offering documents. Past performance is not indicative of future results. Investment involves substantial risk, including loss of principal. RavenRock is a private investment firm and is not affiliated with any U.S. government entity. ©2026 RavenRock Ventures
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RavenRock Operations, LLC
jason@ravenrock.vc
Every venture portfolio has them: software companies with real revenue, paying customers, and no path to the next round. We give their investors a straight read on what the company is worth and what to do next. When a bridge makes sense, we invest deal by deal. We call it Venture Equity.
NOTICE: The information on this website is provided for general informational purposes only and does not constitute an offer to sell or a solicitation of an offer to purchase any securities. Any securities offered by RavenRock will be offered only to accredited investors pursuant to Rule 506(c) of Regulation D and only through definitive offering documents. Past performance is not indicative of future results. Investment involves substantial risk, including loss of principal. RavenRock is a private investment firm and is not affiliated with any U.S. government entity. ©2026 RavenRock Ventures
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