
Backing technical founders rebuilding software and infrastructure for an AI-native world. Email is best: [email protected]
SA | Austin | SF
Joined March 2017
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Backing AI-native founders building the future of software
I’m excited and humbled to share that we’ve closed our third fund at Active Capital: $28M+ to invest in the future of enterprise software and cloud infrastructure.
I started Active Capital seven years ago with a belief: founders deserve early capital from someone who's walked in their shoes. Someone who truly understands the challenges of starting and building a great company. With this new fund, we’re continuing to invest in the kinds of companies I helped build, many of which are building in underdog cities across America.
As an entrepreneur, I’ve helped lead companies through major shifts—from old-school software to SaaS, cloud, and mobile. Today, I couldn’t be more excited to back the next generation of founders who are re-shaping software and infrastructure in the AI era.
The strategy is working. Our first fund, raised in 2018, has already returned nearly 70% of capital, with a total value-to-paid-in (TVPI) multiple—meaning the current value relative to capital invested—now exceeding 4x.
While this is the largest fund we’ve raised to date, it’s still smaller than most funds you’ll read about. When I started Active Capital, I purposefully decided that part of our strategy would be to raise multiple similar-sized, $25M-ish funds—to stay focused, master our craft, and resist the urge to go upmarket. This is a very unique strategy in venture capital as the temptation to raise bigger and bigger funds is extreme.
That said, small numbers add up too. This new fund brings us to over $100M in assets under management, across three similar-sized funds and several individual investments in breakout companies.
Since 2018, we’ve backed 50+ startups across the country, in cities like San Antonio, Austin, Minneapolis, Kansas City, Miami, Atlanta, Boulder, Portland and of course… NYC & SF.
Some of our early exits include:
- Altru, acquired by iCIMS
- Cloudsnap, acquired by Paylocity
- Finmark, acquired by Bill.com
- Makeswift, acquired by BigCommerce
- RemoteTeam, acquired by Gusto
What we invest in:
- Lead or co-lead pre-seed rounds
- $500K–$1M checks in $500K–$3M rounds
- Strong preference for smaller rounds, low burn, and extreme focus on product market fit
- Technical founders, solo or team, building in cities across America
More about Active:
- Pre-seed firm focused on enterprise software & cloud infrastructure
- Solo GP firm & awesome team with 15+ years working together
- Repeatable, similar-sized funds; focused on mastery, not scale
- We’re long term investors–we don’t chase early markups or depend on secondary sales
- Backed entirely by successful founders, families, entrepreneurs, and operators—no institutional capital
I’m especially grateful to our investor base—from former Rackers, to incredibly successful families and entrepreneurs in San Antonio, to founders and friends I’ve met along the way… and of course, plenty of Virginia Tech Hokies. THANK YOU!
If you’re building something bold at the pre-seed stage, let’s connect.
Active Capital retweeted
Today we're launching @agent_relay
Your team’s agents shouldn’t need YOU to copy-paste their conversations.
Agent Relay lets them read each other’s sessions, ask questions, and hand off work across the tools your team already uses.
Keep using the Codex mac app, Claude in the terminal or even tools like Conductor.
Open source. Free to try our cloud.
agentrelay.com
Active Capital retweeted
Daytona is currently the fastest growing company I’ve ever invested in. Congrats on the raise!!
We just raised a $60M Series B at a $1B valuation to build @daytonaio into the Agent Cloud.
@FirstMarkCap led the round, with all key existing investors and angels doubling down.
We're also thrilled to welcome the founders of some generational companies aboard, including @patrickc (Stripe), @tobi (Shopify), @AravSrinivas (Perplexity), @BrendanFoody (Mercor), @oliveur (Datadog), @adamdangelo (Quora) and @ericsyuan (Zoom)
We're a 35-person team. But that's about to change; we're hiring across the board, and we'd love for you to join us.
Active Capital retweeted
$2B in portfolio exits so far this year. Exciting times for our small venture firm.
Active Capital retweeted
Some of the companies that have acquired Active Capital portfolio companies over the years:
- Workday
- Gusto
- Bill
- Superhuman
- Flex
- Paylocity
- Medallia
- Flexera
- Commerce
- Opendoor
- Owner
- Paymentus
- iCIMS
- Workleap
- CallRail
Active Capital retweeted
Huge Congrats to Alex Bovee, @pquerna and the @ConductorOneInc team on the @Workday acquisition.
Active Capital was C1's first pre-seed investor in 2021, and Pat's history with Paul goes back to Rackspace.
Alex called identity as the control plane for people and AI agents years before it was obvious.
Proud to have been along for the ride and fortunate they let us invest!
We’ve signed an agreement to acquire C1.ai, an agentic identity platform for people and AI agents. With C1.ai, Workday will become the identity governance layer for people, money, and agents. w.day/3UsJttH
Active Capital retweeted
I kept watching InstaCloud's project count climb during YC. 30k, then 40k, then 50k.
I reached out to @hanghuang_ . He replied in 2 minutes. Turns out he and his cofounder @tonychang430 compete to answer customers even faster.
Today, InsForge becomes InstaCloud with an $8M seed. Proud to be an investor and in their corner.
We just raised an $8M seed round to kill AWS, GCP, and Azure.
Introducing instacloud.com, the agent-native serverless cloud.
Your team is shipping code like never before. But you're getting caught up in manual, tedious DevOps work trying to deploy it.
InstaCloud provides the serverless compute that lets your services autoscale, with all the infrastructure managed for you.
Agents branch into complete replica environments when working, keeping prod safe and iteration speed high.
And of course, it all works seamlessly with agents through MCP/CLI.
Get off the traditional, legacy cloud.
Start deploying your services on InstaCloud today.
Active Capital retweeted
I’m bullish on our firm @activecapitalvc because we’ve been in the founder’s seat.
My partner and our founder, @patmatthews, built and sold his company to Rackspace, then helped scale it from $300M to $1.5B in revenue as an executive.
He’s made the hard calls and knows what’s at stake.
There’s a reason founders want him in their corner.
Active Capital retweeted
Just funded our latest pre-seed investment. Very excited about this one. A few datapoints:
- $500K first check
- $10M round that closed in weeks
- Repeat founders, SF-based
- Real-time auditory reasoning
- Built for AI in the physical world
We’re averaging one new pre-seed investment per month. If you’re building in our space, please get in touch. Email is best.
Active Capital retweeted
Fathom is being acquired by @Superhuman!
We first invested in Fathom in 2021… before the “ChatGPT moment”... and before every tech company tried to build its own notetaker.
Unlike so many startups from the 2021 era, Richard and team navigated the last five years extraordinarily well.
Fathom is an awesome product that I use every day, and it continues to get better and better.
Congrats to Richard, the Fathom team, and everyone involved. I love the roadmap and I’m pumped for what’s ahead!
Active Capital retweeted
I love this work. I get to back cracked, generational founders solving the world's most important problems.
Working on something but haven't told anyone yet? I want to be the first check.
Writing $500k first checks, 10 investments YTD
DM me the thing you can't stop working on
Active Capital retweeted
I raised a $2M "concept fund" before raising funds from LPs I didn't know. Got to start somewhere...
Many of the great VC firms and solo GPs started out with funds of $10M or less.
These micro VC firms have a risk appetite which is crucial to the industry, and play an important role in seeding risk capital where larger firms cannot.
"Micro VCs play a pivotal role in democratizing access to entrepreneurial finance by allowing ventures to get funding from a new type of investors. Moreover, micro VCs encourage more kinds of limited partners to access the VC industry."
- Micro VC (2022)
Unfortunately, the associated regulatory costs make operating at this scale incredibly difficult in the UK.
Admin and compliance often consumes about $1.4M of a $10M UK fund, versus just $450k in the US.
As a result of this high cost, the median fund size in the US was $20M in 2024, in the UK (with just 3% of the volume) it was $88M.
So, the UK not only has lower total venture capital volume, it also has fewer small funds — the worst of both worlds.
This is a major bottleneck, but there is a fix. If you're interested in hearing more, drop me a DM.
(Credit to @cupazhou and @samhuleatt for the graphic below, from The Side Letter.)
Micro VC paper: eiexchange.com/api/submissio…
Active Capital retweeted
Insane shipping speed + innovation in the space =🚀🚀🚀
@ycombinator Demo day watch out!
We’ve been quietly building something inside Datoric.
Today, we’re launching Datoric Research, with a new Head of Research who will be leading the effort.
Speech + paralinguistics. Egocentric video understanding. Automated annotation + QA. Fraud detection. Data diversity.
Models, benchmarks, datasets, and research coming soon.
First release shortly.
Active Capital retweeted
Just funded our latest investment:
– $500k check
– Two technical founders
– SF-based
– Custom, security-first training data
– Seven figures in revenue the last 30 days
That's eight investments this year and we're backing at least one new team every month.
Active Capital retweeted
Active Capital exists to write first checks and put founders in business.
If you're building AI-native business software or infrastructure, we want to be your first yes.
DMs open.
Active Capital retweeted
Landed back from SF Thursday night.
Signed a $500k SAFE Saturday night with a founder I met on the trip.
More on this one soon.
Reminder: we write $500k first checks into the most technical founders & ambitious founders with an irrational level of commitment to building something great.
Active Capital retweeted
Some good insights in here. A few observations from my experience in case they’re helpful to other emerging managers:
1/ We’re diversifying as much as ever. Picking winners at pre-seed is really hard. But we back founders really early, and when we’re able to build strong relationships, there are almost always opportunities to put more capital to work as the winners emerge over time.
2/ We’ve had one fund returner (multiple times over), and I can attest… they’re really hard to come by. We’ve also had a lot of solid exits that return 10-25% of a fund. Those are great outcomes, but it takes a lot of them to add up to strong returns for investors.
3/ I’ve always told our LPs we’re going to stay small and raise multiple similarly sized funds. We’ve iterated on a lot of things over the years, but not this. The temptation to raise bigger and bigger funds is huge, but we’re staying disciplined. When we have breakout winners, we’ll raise SPVs. Our LPs have really liked this model.
4/ We’ve been fortunate to generate solid DPI even without exposure to the $100B exits or trillion-dollar IPOs. I think we’ll have a few of those one day too though!
5 & 6/ I didn’t come up through the traditional apprenticeship model, and maybe that’s one reason we’ve had more success raising from builders, operators, and entrepreneurial family offices than institutions. I’m incredibly grateful for all of our investors!!
a few insights after talking to a bunch of VCs and LPs this week:
1/ a large number of EMs are trying to build concentrated portfolios without any real rationale behind it. Mostly they're either chasing the prevailing narrative ("we're in an era of concentration now!"), or bending to LP mandates that demand high-conviction portfolios of just 10-15 positions and won't write a check otherwise, or simply copying the mega-fund playbook – funds that concentrate their own bets in high-capex AI labs as a way to deploy the billions they've raised. But copying the model without understanding the reasoning behind it is destructive, and very few managers can actually execute a concentration strategy well.
2/ even among the best seed investors historically, only a small share of deals ends up returning the fund. One GP pointed to USV as an example, where that figure was around 7-8%. For a strong emerging manager today, his estimate was closer to 4-5%. His core argument: in the AI era, that picking rate at seed will only get worse, since the number of companies is growing and the pace of disruption is accelerating. The implication is that LP appetite for concentration may simply be out of step with what's actually optimal portfolio construction for most seed managers.
3/ many GPs are aggressive about growing fund size from Fund I to Fund II, or Fund II to Fund III, and few can really justify it. If you raise a $25M fund and then want $50M, then $150M – that's a major red flag for LPs unless there's a clear rationale. Scaling up fund size forces one of three tradeoffs:
> you dilute focus by moving into later rounds (seed to Series A)
> or you increase the number of portfolio companies (without the operational bandwidth to actually manage that many, or the ability to physically write that many checks within a 3-4 year investment period, given brand constraints)
> or you push for higher ownership (which isn't always feasible either, since it means either leading rounds or hunting for deals where you can pay less which nudges managers to optimize for price over deal quality)
4/ the market got very excited about the upcoming SpaceX mega-IPO, but DPI from that exit hasn't really hit yet, and the liquidity window probably won't open before year-end. It'll likely take until early next year, along with a few more IPOs, before sentiment fully shifts – though plenty of mega-platforms are already raising billion-dollar funds off the back of it (e.g. Menlo, which raised $3B thanks to Anthropic bet). But most LPs, though, are already planning their budgets around early 2027.
5/ a separate, interesting pattern: some LPs and FoFs are increasingly looking past a manager's "brand" and toward their apprenticeship lineage instead. One LP I spoke with framed it as a bet on elite apprentices – it matters less whether someone formally came out of Sequoia or Benchmark or another tie-1 platform fund, and more whether they worked closely under one specific strong partner and absorbed their taste, judgment, network, and actual underwriting craft. The logic is that VC is still fundamentally an apprenticeship business, and if an EM was genuinely "under the wing" of an exceptional investor, the LP is getting a piece of their whole school of thought.
6/ one more LP insight I heard more than once: builders tend to convert better than institutional allocators. People who've built companies themselves generally have a better feel for what a small VC fund actually offers (access, judgment, network, founder quality) and are more willing to back a manager even without full institutional packaging. Institutional allocators default to "no" more often as their decision-making is more inertia-driven and career-risk averse, so it's simply easier to go with a familiar brand than back a niche or emerging manager, so EMs often find traction faster with builders, operators, and entrepreneurial FOs first, rather than trying to look "institution-ready" to everyone right out of the gate.
Active Capital retweeted
New algo, new request for startups.
We write $500K - $1M checks.
Backing in AI-native founders building the future of software.
We are founders turned investors.
Doing 1 new deal each month.
Incredibly ambitious ideas only.
Active Capital retweeted
Just sent our monthly LP update. We’ve invested in 25 companies over the last 24 months. Still have ⅓ of fund to deploy. Should be a fun second half of the year!!
Active Capital retweeted
We just committed 500k to a founder I’ve backed twice before. Beyond excited to back her again.
Active Capital retweeted
Just wired our fifth pre-seed investment of 2026:
– $750K lead check
– Three founders out of Michigan Medicine + Johns Hopkins
– AI operating layer for hospital transformation
– Live pilots & conversions in some of the largest health systems in the world
– Eyeing relo to SF or NYC
Reminder: we're backing at least one new team every month with $500K to $1M checks.













