2025 was a big year for the team at Redbud. If 2024 was a year of building, 2025 was a year of growth. We grew nearly everything: network, portfolio, brand, team, and AUM. We welcomed two new team members, Kiley Grimes (Head of Ecosystem) and Hemkesh Agrawal (Head of Engineering), to help our portfolio and ourselves move faster than ever.
At Redbud VC, building has always been foundational. In 2025, we focused on scaling the parts of that foundation that most directly compound for founders and Limited Partners.
Over the past year, we’ve:
Reviewed 3,500+ companies, up 16% from 2024
Invested in 13 companies
Made 300+ customer, investor, and talent introductions to our portfolio companies
$115M raised by our portfolio companies with $93M post our investment
Crossed 15,000 subscribers on the Redbud VC Newsletter, up 6% from 2024
Joined over 700+ attendees at our events
Broke 2.5M impressions across our Website, Medium, Linkedin, and X, up 160% from 2024
Received a 42x markup, resulting in top decile performance for a 2023 vintage
Issued our first distributions to LPs from Fund I
Portfolio Highlights:
OneImaging closed a $38M in funding led by VY Capital
Transend hit profitability and surpassed $7M ARR
Trially closed a $4.7M Seed round led by Flyover Capital
8 companies closed healthy undisclosed Seed rounds
SafeRide closed a Seed+ round a month after we invested
Mattoboard closed a $2M Seed round led by Acrobator Ventures
dScribe joined the S25 batch of YC and closed a healthy Seed round post demo day
4 Founders were named to the Forbes 30u30 2025: Eunice Wu & Can Uncu, Co-Founders of Asepha, and Mihailo Bozic & Dylan Gibbs, Co-Founders of Migrate Mate
Investments:
We invested in 13 pre-seed startups across the US and Canada in 2025. We take pride in driving our own convictions in the companies we invest in, and when we say generalist, we really mean it. Take a look at our investments from 2025 below ⤵️
Keysquare (First VC)
Fixed income trade automation and analytics
New York, NY | Khai Hong, Tiffany Hu, Saad Munir, Jitesh Vassa | Fintech | Website
Stealth
Los Angeles, CA | AI/ML
BalanceHQ (First Check)
CFO tools for school districts and non-profits
Columbia, MO | John Larrick, Dr. Ben Latimer | Fintech | Website
Bolster
The modern way to run a construction company
Calgary, Canada | Mike Bignold | Contech | Website
Focus (First Check)
Affordable crowd-sourced case evaluation
Columbia, MO | Jill Harper, Ben Zalasky, Ron Netemeyer | Legal Tech | Website
Mirala
A single, unified global network for asset tracking
Los Angeles, CA | Dan Hart, Matt Hughes, Ted Meyers | Hardware
Asepha
AI workflow automation for pharmacy
Toronto, Canada | Eunice Wu, Can Uncu | Health Tech | Website
Migrate Mate
Unlocking jobs & visas for millions of immigrants
New York, NY | Mihailo Bozic, Dylan Gibbs | Legal Tech | Website
Stealth
Kansas City, MO | AI/ML
Stealth
San Francisco, CA | Health Tech
Routesense (First Check)
Real-time visibility into merchant health
Salt Lake City, UT | Stephen Martin, Colin Martin, Robert Matthews | Fintech | Website
High Degree (First VC)
Steam-based soil disinfestation for specialty crops
San Francisco, CA | Austin Bowie, Eric Brown, Steve Fennimore | AgTech | Website
Events:
Missouri Startup Weekend - April 2025
This year marked the 13th annual Missouri Startup Weekend, and the fourth time Redbud VC hosted the event. We kicked off the weekend at the EquipmentShare HQ with over 150 participants ready to take on the challenge of building a company in 54 hours.
We had a record 63 participants pitch their initial startup ideas on Friday night, and 11 teams formed around the top concepts. The teams then spent the weekend focused on building: speaking with potential customers, developing MVPs, and conducting market research. This year, we curated 12 high-caliber mentors to work with the participating teams on Saturday, including:
Levi Mallot, CTO at Weave (Series B)
Ketul Patel, Investor at Headline ($100M+ AUM)
Marc Bernstein, CEO & Co-Founder of Balto (Series B)
Bess Goodfellow, Partner at Hyde Park Angels ($100M+ AUM)
Phil Renyolds, CEO & Co-Founder of DevStride, previously BriteCore ($100M raised)
and many, many more….
We also brought together a panel of judges composed of successful founders and investors across the region, including:
Willy & Jabbok Schlacks, Co-Founders of EquipmentShare
Jyothi Vallurupalli, Investor at Lightbank
Lori Coulter, CEO & Co-Founder of Summersalt
Wade Foster, CEO & Co-Founder of Zapier
MOSW has always been a weekend for builders, which is why we wanted to build something new in 2025! So, we introduced the Sprint Track. This new track invited four established pre-seed/seed companies to join us for the weekend at ESHQ. The track provided the teams with a dedicated, focused space to be heads down, access to exclusive workshops and mentoring sessions, and a chance to share what they are building with the broader MOSW community. Our Sprint Track companies were:
dScribe AI, Kansas City, MO
Balance HQ, Columbia, MO
Vendoor, Cape Girardeau, MO
Replacement Cars, St.Louis, MO
We crowned three winners at Startup Weekend in 2025:
1st Place Winner of $45k Grand Prize: Focus - Affordable crowd-sourced case evaluation
Press Coverage sponsored by Relevance
6 months of Post Launch Support sponsored by Redbud VC
$5k in Legal Formation sponsored by Transitions Law
$15k in Branding & Design Package sponsored by Bullpen Design
$15k in MVP Development sponsored by Aviron Software
$10k Cash
2nd Place: GoldenHome Share - An Airbnb-style platform for long-term stays with older hosts, discounted in exchange for household help.
3rd Place: SiteScan - Quality control and safety software using AI image-processing for construction and civil sector projects
Builders & Backers - November 2025
Builders & Backers is an event designed to unite leading executives, investors, and entrepreneurs who are redefining the future of the built environment. We hosted Builders & Backers alongside Suffolk Tech and C-Tech Club in Boston, MA, to kick off Boston Built Week. We brought together 150+ construction/proptech founders, investors, and industry execs from 14 states for >3 hours of curated networking and a panel featuring the industry’s best.
Main Street Summit: Startup & Venture Track - November 2025
For our final event of the year, we hosted The Startup and Venture Track at The Main Street Summit. The Main Street Summit brings over 1k operators, owners, and investors to Columbia, MO, for a three-day festival. We had over 20 Redbud founders make the trek to COMO, and many LPs attended MSS for 3-days of T-1 networking, programming, and activities.
We hosted 10+ venture track exclusive speaker sessions and main stage events, including:
Purpose & SaaS with Kristen Anderson, Partner at High Alpha
Consumer Conviction: Building Hallow with Co-Founder Erich Kerekes
Investing With Intention with LeftLane, Motivate VC, and Redbud VC
Three LP Lenses: How Capital Really Chooses Managers
Oh yeah, and we also had some exclusive activities for track attendees. Some of our favorites:
Evening Cocktail Class at LeMullier
Poker Night at 6 Mile Distillery hosted by Angel List
Founders & Funders Breakfast at Sage Cafe hosted by EquipmentShare
To close out MSS, we hosted our founders & friends at the University of Missouri’s Memorial Stadium at the Bunker Club to celebrate a great event, year, and a few other unannounced surprises 😉
Communities + Media:
We crossed 2.5M Impressions across our Website, Medium, LinkedIn, and X this year, 2.5x our impressions from last year! A few highlights from our brand & communities throughout the year:
Launched our new Website & brand refresh, thanks to our friends at Bullpen
The Redbud VC Newsletter broke 15k subscribers.
Missouri Governor Mike Kehoe appointed Brett to join the Board of Directors of Missouri Technology Corporation
Brett joined the board for InvestMidwest
Podcast features on AllStar Allocator, SaaS That App, Diligent Observer
Travel:
This year took our team from coast to coast, talking to founders, investors, and communities about what we’re building at Redbud.
January →
Bluestein Ventures & Chai Ventures Ecosystem Connect | Chicago, IL
April →
Missouri Startup Weekend | Columbia, MO
Invest Midwest | St.Louis, MO
Lightning | Nashville, TN
Redbud Ecosystem Gathering | Kansas City, MO
May →
Lofty Ventures Spring Party | Chicago, IL
NWA VC Immersion Series | Bentonville, AR
June →
EVCA Breakfast | Chicago, IL
Artemis Fund Female Founders & Friends Coffee | Chicago, IL
Rise of the Rest Founder Fly In | Chicago, IL
Redbud Ecosystem Gathering | Kansas City, MO
July →
Tech Chicago Week | Chicago, IL
Redbud Ecosystem Dinner | Columbia, MO
Redbud Ecosystem Dinner | Cape Girardeau, MO
August →
Emerging VC Dinner hosted by HPVP, Mairs & Power, SVB, and Cooley | Chicago, IL
Redbud Ecosystem Gathering | St. Louis, MO
September →
Capital Collective Female Founders & Funders Dinner | New York, NY
Chingona Ventures Hispanic Heritage Month Founders & Investors Taco Dinner | Chicago, IL
Drive Capital "DriveHouse" Founders End of Summer Showcase | Chicago, IL
TAM by Drive Capital | Austin, TX
October →
Afore’s Pre-Seed Summit | San Francisco, CA
Cherub Investor Dinner | Chicago, IL
November →
Builders & Backers | Boston, MA
Main Street Summit | Columbia, MO
MidxMidwest | Kansas City, MO
Personal Updates:
Willy & Brett spent most of 2025 on a “Missouri World Tour” raising Redbud Fund II (details coming 👀). Outside of Redbud, Willy & Jabbok celebrated EquipmentShare’s 10th anniversary and expanded their HQ with a new Technology & Development Center. Brett finally made it on a very overdue honeymoon. Off the road, he was mostly renovating his house in COMO and spending time with his wife and two French bulldogs, Tom & Henry. Maria endured her first Chicago winter and still stayed. She spent lots of time trying new restaurants (63!) and traveled to 11 states and one new country this year.
2026 Predictions:
Our Year in Review wouldn’t be complete without some of our predictions for 2026. Here’s how our 2025 trends shook out:
IPO window opens, but many companies will have down rounds to their latest private market valuation. ✅
Mega funds start buying early-stage emerging manager funds, providing liquidity to LPs. ✅
Lackluster exit multiples from depressed valuations and over-raising will further decrease distributions to early-stage funds, decreasing Fund III and IV raises ✅ and pushing multi-stage funds away from Pre-Seed, opening a window for new and existing managers on Fund I or II to take advantage of reasonably priced deals.➖
OpenAI will be surpassed as the leading AI company. ➖
Valuation reckoning as IPOs and M&As heat up at much lower valuations. ❌
YC companies will have to give on the $15M minimum valuation as many struggle to raise post YC and/or raise flat round 12-18 months later. ❌
2026 Predictions:
The Series A crunch from 2024 will have permanently reshaped Seed financing: extreme valuation dispersion, hyper-competitive rounds, as investors push to hit ownership targets earlier and earlier.
With market performance increasingly propped up by a small concentration of AI-native companies, the AI bubble pop is coming.
OpenAI’s cash burn, coupled with spending commitments they may not be able to fund, mirrors the behavior of late-stage Enron and will result in a similar outcome.
A strong consumer-driven push toward “return to human” experiences. Community, presence, and authenticity, as buying power corrects for the pendulum swing of two years of “AI-in-everything.”
Nuclear has a comeback to sustain the long-term energy usage of AI
The hyper-growth AI companies will experience flat or declining revenue, with continued pressure on margins
“AI-first” startups will underperform “AI-second” startups
Vertical SaaS returns to being the highest-alpha category
“Founder-market fit” will matter more than founder pedigree
