We’re happy to share the latest in AltsTech’s series profiling how investment managers are using AI, tech, and analytics to generate alpha. We’re fortunate to interview Ryan Gaines, Founder of N6 Ventures.
David Teten: Please give us an overview of your firm.
Ryan Gaines: N6 Ventures is a $5M seed-stage venture fund based in Palo Alto, backing US-based AI application companies at seed. We write checks of $100K–$500K, focused on vertical AI that replaces entire workflows rather than just aiding them, and businesses whose data flywheels deepen their competitive moat over time.
What separates us from most seed funds is how we source and evaluate companies. I also run N6 Finance, an AI + human CFO platform for venture-backed startups. We set up finance infrastructure for early-stage AI companies from day one, giving us direct, ongoing visibility into how founders actually operate before they ever begin fundraising. That changes the quality of information we’re working with when we decide to invest.
We look for domain-obsessed founders deploying AI against sector-specific, painful workflows. Thin wrappers, undifferentiated copilots, and teams without domain depth are what we avoid.
Our network includes 200+ active founders in the AI application space who have collectively raised $1.1 billion over the past three years. By the time a company opens a seed round, we’ve often known the founder for 6–18 months.
David Teten: Your model sounds quite similar to how, when I was a Partner at ffVC, we incubated Graphite Financial as an outsourced CFO service. We eventually spun that out, in part to mitigate conflicts of interest, and it was acquired by Kiwitech. Who are your peers/competitors, and how do you differ?
Ryan Gaines: At seed, we overlap with generalist micro-VCs and AI-focused seed funds. There’s also a growing cohort of solo GPs who’ve launched AI-focused seed funds over the past two years, many with strong technical backgrounds.
Our difference is being able to partner on an operating level and help our founders solve real problems around hiring, fundraising, burn management etc. Even for companies where we invest, but don’t take on an advisory role, we’re often able to connect them to the right investors for future rounds.
David Teten: What’s your background? How and why are you in your role today?
Ryan Gaines: I started in investment banking at Lazard in M&A advisory, then moved to Trian Fund Management as an investment analyst doing activist investing. That background gave me a rigorous framework for understanding what separates operationally excellent companies from struggling ones, a discipline I’ve applied differently but consistently ever since.
About ten years ago I founded N6 Finance because I kept seeing the same problem: early-stage founders were brilliant at product but flying blind on finance. N6 Finance grew through referrals into a platform serving dozens of venture-backed companies at a time.
What I didn’t anticipate was how clearly you can see which companies are actually working when you’re inside their numbers. It sounds simplistic, but founders who executed against their plan, made clear decisions, and saw real pull from the market are outperforming those that aren’t. N6 Ventures is the direct extension of that insight, allowing us to invest in the winners using “inside information.”
David Teten: There’s an obvious potential conflict of interest between your role as investor and your role as part-time CFO. What policies do you use to mitigate these?
Ryan Gaines: You’re right that the dual role creates potential for conflict of interest, and I actively work to reduce both perceived and actual conflicts. First, both relationships are fully disclosed at the outseT. Also, when I invest in a company where I serve as fractional CFO, I do so only on terms set by the board or an independent lead investor, with no preferential pricing. The investment requires board consent with the conflict noted in the minutes, and my CFO compensation stays a fixed retainer unrelated to fundraising or valuation.
Beyond the deal itself, I keep the roles from bleeding together. What I learn as CFO doesn’t inform fund decisions about competitors or comparable companies, and I don’t take CFO engagements with companies that compete with existing portfolio companies. That said, investing alongside CFO clients can genuinely align interests, combining skin in the game with operational understanding, but only if the governance is tight enough to avoid potential conflicts.
David Teten: What are the tools you’re using for your front office: sourcing, LP relations, investing analysis, etc.? What are the strengths and weaknesses of these providers?
Ryan Gaines: Decile Hub is our deal flow CRM. It’s purpose-built for relationship-driven workflows, and the automatic logging of emails and meetings reduces the manual entry burden considerably. The weakness: the analytics and reporting layer is fairly shallow if you want to build custom queries on your pipeline.
All investment memos and notes live in Notion. We use a structured template for every serious opportunity, which creates a consistent record of our thesis at the time of decision.
For market research and competitive context, we use Crunchbase Pro for early-stage deal discovery and PitchBook for deeper funding history and investor activity tracking. PitchBook is expensive for a fund our size, but the data quality is hard to replicate on key questions.
We currently do LP communications and quarterly reporting manually, but would look to onboard a tool like Visible.VC in the future.
David Teten: What are the tools you’re using for supporting your portfolio companies? What are the strengths and weaknesses of these providers?
Ryan Gaines: The most important tool we offer portfolio companies is N6 Finance itself. When we invest, we often bring the company into our platform, building their financial model, setting up their accounting infrastructure, and preparing their next fundraise materials.
For day-to-day communication, we maintain a Slack channel or text thread with each portfolio company. Founders can reach us quickly without it turning into a formal meeting request.
We also make specific tool recommendations based on what we observe in the financials. If burn is running high due to untracked SaaS spend, we’ll point founders to Ramp for spend management. We’re also exploring some new tools specific to AI spend management (e.g. Superpenguin).
David Teten: What are the tools you use within N6 Finance, i.e., to provide standard outsourced CFO services?
Ryan Gaines: At N6 Finance, I run a lean stack that covers the core CFO workflow. QuickBooks Online is the accounting ledger for most clients, with FinOptimal layered on top to automate reconciliation and accruals. I also use Double to manage the close process with my team. Google Sheets does the heavy lifting on modeling, forecasting, and ad hoc analysis. I use Carta for cap table management, 409A valuations, and equity admin. I’m a big fan of Ramp and use it with almost all of my clients for bill pay, credit cards, and spend management. And I use Claude extensively for drafting board materials, stress-testing model assumptions, and summarizing diligence documents. The throughline is automating the mechanical work so I can spend time on the judgment calls that actually move the business.
David Teten: What technologies/databases have you found helpful in winning LPs? (I wrote about this in Why Isn’t Sales As Efficient As Online Dating and Fundraising hacks for VC and private equity funds.
Ryan Gaines: Our LP base has grown primarily through warm relationships. For example, former founders we’ve served through N6 Finance, legal and finance professionals who’ve seen our work firsthand. Outbound LP development hasn’t been the primary driver, so our tooling is lightweight.
LinkedIn and Crunchbase are useful for researching prospective LPs before meetings to understand their background, relevant portfolio exposure, and shared connections.
For sharing materials, we use Decile Hub, which allows us to know whether someone opened the deck and how long they spent on each slide
David Teten: What tools do you find helpful for expediting due diligence?
Ryan Gaines: Our most differentiated diligence capability isn’t software; it’s the operational relationship we’ve already built with the company through N6 Finance. By the time we’re making an investment decision, we’ve often seen 6–12 months of financial data, watched how the founder handles runway conversations, and have a real view of the customer base through invoicing patterns. Most of what traditional diligence is trying to learn, we already know.
For reference checks, we use LinkedIn to map mutual connections across a founder’s prior employers and investors, then conduct calls early in our process rather than as a final gate. References are most useful before conviction forms, not after.
For technical evaluation of the AI stack, model architecture, vendor dependencies, data practices, we draw on a network of technical advisors.
David Teten: What are the tools you’re using for your middle office: tracking, risk management, etc.? What are the strengths and weaknesses of these providers?
Ryan Gaines: For portfolio tracking, we maintain a master dashboard in Airtable. Each company reports monthly revenue, burn, runway, headcount, and relevant model-specific metrics. The data is entered manually after review calls, which is intentional, the manual review forces us to stay close to each situation rather than treating dashboards as a check the box exercise.
Carta handles cap table management and secondary transaction tracking. It’s great because so many companies are on it, but it doesn’t come cheap.
David Teten: What are the tools you’re using for your back office: settlements, records maintenance, accounting, human resources, etc.? What are the strengths and weaknesses of these providers?
Ryan Gaines: Decile handles fund administration like LP capital accounts, capital calls, and distributions. Our fund counsel manages entity-level legal work. For accounting and audit prep, we work with an external fund administrator and accounting firm rather than attempting to build it internally. A $5M seed fund doesn’t need complex back-office setup.
K-1s and fund taxes go through our accounting firm. For day-to-day operating expenses and vendor payments, we use Ramp.
HR is minimal. As a solo GP with a lean structure, most ‘HR’ is keeping contractor agreements and service relationships organized in Google Drive. The overhead of dedicated HR software isn’t justified at this scale.
David Teten: A huge amount of valuable data flows through your pipes. What are you doing to capture that data and mine it? Can you share any patterns you have identified?
Ryan Gaines: The unique data asset in our model is the financial operating data from N6 Finance. Over ten years, we’ve worked with dozens of venture-backed companies across pre-seed through Series B in multiple sectors. That creates a longitudinal dataset that most investors don’t have access to.
One concrete pattern we’ve observed: companies that hit retention problems almost always end up making a significant pivot at some point in the future, but most wait too long to make a big change.
We don’t yet have a formal data warehouse, but building a more systematic way to mine this dataset is one of our medium-term priorities.
David Teten: Do you see any room to use AI to exploit your dataset? If so, what are you doing to move that forward?
Ryan Gaines: Yes, and we’re in early stages of building toward it. The most immediate application is using AI to flag anomalies in portfolio company financials faster. We’ve been experimenting with LLM-based summarization of monthly financial packages to surface the questions worth asking on the review call.
The longer-term opportunity is using N6 Finance’s aggregate dataset to build seed-stage benchmarks that are grounded in actual operating data rather than reported metrics. ‘What does healthy burn look like for a B2B AI application at $100K MRR’ is a question we can answer from our data in ways most seed investors can’t.
David Teten: An obvious model here is Scale VC’s GTM Benchmark tool. What other tools do you recommend for benchmarking?
Ryan Gaines: Some benchmarks that I rely on regularly are:
- Carta for valuation benchmarks based on company size / stage / sector
- AngelList to benchmark cash comp and equity grants
- Benchmarkit.ai for general SaaS KPI benchmarks
David Teten: What are the most creative or unusual ways you’re using AI & analytics in your organization?
Ryan Gaines: One thing that’s been concretely useful is before a first meeting with a founder, I synthesize everything publicly available about the company and ask an AI model to identify open questions I should probe. It surfaces things I might miss in a 30-minute prep and produces better first meetings. I’ve found the questions that come out of that exercise are more specific than my instinctive prep questions tend to be.
David Teten: What is your prompt for doing that?
Ryan Gaines: I have a first meeting with [FOUNDER NAME], a founder at [COMPANY NAME]. Before I go in, I want to be as prepared as possible.
Please do the following:
- Research the company thoroughly — search for everything publicly available: their website, LinkedIn, Crunchbase, any press coverage, product reviews, job postings, founder backgrounds, recent funding announcements, social media presence, and any interviews or podcasts the founder has done.
- Synthesize what you find into a tight briefing covering: what the company does and for whom, their business model (as best you can tell), traction signals (funding, customers, growth indicators), the competitive landscape, and anything notable or unusual about the founding team.
- Identify the open questions — this is the most important part. Based on what you found (and what’s conspicuously absent), generate a list of specific, probing questions I should ask in the meeting. These should not be generic VC questions. They should be specific to this company, this founder, and this moment. Flag things that seem inconsistent, unclear, or that warrant deeper investigation. Prioritize questions that a founder might not have a polished answer to.
Format the output as: (1) a brief company snapshot, (2) a founder snapshot, (3) key observations and flags, and (4) the question list ranked by priority.
David Teten: What are your unmet technology needs? Places in your firm where you’re seeking a solution and haven’t found an appropriate one?
Ryan Gaines: Seed-stage portfolio benchmarking. There are tools that show funding raised or headcount growth, but the metrics that actually matter at seed like early retention cohorts, payback period, revenue quality, burn multiples at $50K–$500K ARR aren’t well served by existing products. We’ll likely end up building this manually using our own N6 Finance data, and maybe open it up outside of our ecosystem at some point.
David Teten: What processes are you focused on improving?
Ryan Gaines: The process I think about most is formalizing the handoff between N6 Finance and N6 Ventures. The two businesses share infrastructure, the same founder relationships, the same financial data, the same team, but the workflow for converting a finance client into a live investment opportunity is still informal. I know a company well enough to invest, but the moment I decide to act on that, I switch from “CFO brain” to “investor brain” and those two modes of engaging aren’t yet connected by a clean process. I’m building a more systematic way to flag when a finance client should move to a formal investment review before a round opens.
Another process I’m working on is getting earlier warning out of portfolio financial data. Right now I review company financials monthly and catch issues when they’re already visible in the numbers. I’m finding ways to build leading indicators that can flag issues in real time.
David Teten: For example, at ffVC, we used metrics like “Months of Cash Remaining” to alert us to firms that were entering triage mode.
Ryan Gaines: Months of Cash Remaining is a core metric that we monitor as well (assuming no additional revenue growth). Slowing collections is usually something that can quietly go unnoticed if not monitored closely, so we track A/R balance and days cash receivable rigorously.
We also have cash balance flags set up in their banking system to alert us if cash drops below a certain threshold in real-time.
I also strongly recommend my clients monitor Net Revenue Retention. I find that most companies only calculate it before fundraising, but it should be a core metric for nearly every software company. It’s not a good sign if ARR growth is high, but NRR is low, because it means that customers are buying the product then not sticking around.
David Teten: As an avid AI user, what the prompts that you use most often?
Working with multiple companies at once can be challenging, especially if there are urgent requests that come up at the same time. One of my favorite prompts that I use with Gemini twice a day is: Review all of my emails and calendar and proactively suggest top 5 risks, things I may have forgotten, and/or urgent tasks that need to be done. It helps me prioritize my work and make sure I’m not missing anything.
