Happy Tuesday,
If you're receiving this for the first time, we likely had the pleasure of connecting sometime during Q4 2025. We're glad to have you in the loop.
This email is designed to share key progress updates and insights from our work. You can browse the last five years of updates here. If you'd prefer not to receive future updates, you’re welcome to unsubscribe at any time using the link at the bottom.
In this update, we'll cover the following:
Chisos LLC Updates
Actively deploying capital
New Golf Fund
New Co-GP Fund
Investment portfolio updates
New Investments
Portfolio updates
Chisos LLC
Actively Deploying Capital
In Q4, we made 4 new investments, bringing our overall portfolio to 104 total investments (as of 12/31/25); 13 in Fund I, 56 in Fund II and 35 Balance Sheet investments. We currently have ~$1M in dry powder that we will be deploying over the next few months at a pace of two to five investments per month.
New Fund Initiatives
Chisos Golf Fund
We didn't set out to start a golf strategy.
It started the way our other themes have started. We were underwriting athlete opportunities and kept running into people from the golf world. Players, coaches, agents, trainers, sponsors. Different conversations, same story underneath.
A lot of golf careers don't fail because the player isn't good enough. They fail because the player runs out of runway.
Golf is expensive right when the outcome is most uncertain and the upside is most asymmetric. Travel, entry fees, coaching, training, physio, equipment, time. If you have support, you can take the reps and shots you need. If you don't, you end up making short-term decisions just to stay alive. You can feel the talent in the room, and you can also feel the financial pressure shaping their choices.
That's what made us take a closer look.
As we've dug in, a few things stand out:
The people pursuing golf are unusually high quality. More mature, more self-directed, often higher earning potential than the average athlete profile.
The upside is real if they break through. Golf has a step-change when you reach the next level. Earnings, sponsorship, and brand recognition can jump fast.
The sport has real believers. Golf fans and golf capital are passionate. When someone's in, they're really in. That creates momentum when you have the right structure and team.
Before we launch a dedicated fund, we are working on two primary tasks:
Finalize 2 to 4 pilot investments. We’re already in conversations with multiple players and expect to select a small initial group where the fit, the plan, and the upside are all real.
Build a team that earns immediate credibility. We already have 3 to 4 names in the mix who are deeply knowledgeable and well connected in golf. We’re continuing to add the right people so that when we go to market, we show up with super-credibility.
If you know someone who fits either side of this, a standout player who is underfunded but has a real path, or a high-integrity golf operator, athlete/media name, or finance person with serious golf ties, reach out.
Crowdsurf Co-GP fund
In Q4, we began working with Crowdsurf as partners to co-invest and co-syndicate deals. In Q1 we decided to explore a new Co-GP fund focused on backing exceptional individuals with strong near-term earning power and clear paths to equity upside.
What’s different here is leverage: instead of Chisos doing everything ourselves, we’re pairing our underwriting and structuring playbook with a partner that can help drive broader distribution, high quality collaborations, and operational support. This is part of a bigger push to partner with aligned operators and platforms where we can do more deals, with better sourcing, and less friction.
If you’re an accredited investor who likes the “invest in the person” approach and wants exposure to a concentrated, thesis-driven portfolio, reply to this email and we’ll share more context as the fund takes shape.
Chisos Investment Portfolio Updates
Chisos LLC Balance Sheet
35 Total investments (as of 1/28/26).
4 new investments in Q4 2025:
Paintco Labs (website not launched)
Chisos Capital Fund II - ($2.01mm; closed August 2023)
Fund II is fully deployed with 56 investments. Some notable portfolio updates include:
Arvist and Ink’d Greetings, both backed by institutional venture capital firms, reported strong progress at the end of year. They continue to focus on new customer acquisition, scaling their internal resources and revenue growth.
Companion Candles had an excellent Q4 and ended the year with 2x YoY growth as they continue their split GTM in specialty retail and D2C from their website. Partnerships and collabs are giving them excellent exposure.
Rocco Finance the paycheck advance app achieved record revenue and net profit. They continue to scale mostly bootstrapped and with very disciplined financial controls.
JumpShops has been navigating a changing and evolving landscape in the influencer ecommerce space. This summer they pivoted their offering and billing strategy and this has resulted in much higher retention and LTV; MRR, Commissions earned, and affiliate referrals are all up 200%+ YoY .
Equipcast, the AI-enabled DigiEngineer™ Platform continues to secure interest from large infrastructure projects.
Vestr has expanded their trading and social finance super app to add educational frameworks which opens the high school education market. This answers state based requirements for student financial education. This represents a GTM pivot from B2C to B2B (public schools) and serves as an exciting seeding strategy for keeping the young students as customers after graduation.
Two Spoons Creamery had a transitional year based on having to change their production and fabrication vendor. They also moved away from D2C and are now in Sprouts and in discussions with Safeway. They are receiving strong demand signals as the first Zero Sugar and Protein enriched (GLP1-friendly) ice cream.
Chisos Capital Fund I - ($500k; closed January 2021)
Fund I is fully deployed with 13 investments. 5 companies are still active. Notable updates:
Re-nuble under new leadership, made significant product channel sales changes away from government accounts and towards private markets, and delivered their first profitable quarter.
Redactable continues to scale legal and healthcare markets whilst executing renewals of large DoD contracts.
Vizen Analytics has had some promising breakthroughs with POs for two customers, and a pipeline of later stage deals that puts the company in a position to capitalize on the AI narrative to raise additional growth capital.