VentureSouth Summit 2026 recap
The 10th Annual VentureSouth Summit, February 2026, is now in the books!
Over two days last week, over 200 people – VentureSouth members, portfolio companies, team, a few lucky guests, and two lucky strangers who stole our beer -- enjoyed the full range of VentureSouth content. Here’s what we got up to.
Day 1 – Portfolio review
Kicking off at Greenville’s premier coworking space, Flywheel Coworking, a standing-room-only crowd took a tour of ten of VentureSouth’s portfolio companies.
These companies had previously raised early-stage investment from VentureSouth’s angel investing members and funds (and others), and kindly dropped by to share updates on 2025 performance, their plans for 2026, their views on exit strategies and timetables, and their “asks” for investors. For several, the ask was “please invest again”! Open rounds tally: +9
Day 1 – Party
Angel investing is a contact sport best done in teams and with friends. As VentureSouth covers a southeastern footprint, our members in Chattanooga don’t regularly meet our members in Charleston, or members from Greenville…our members in Greensboro, and so on.
Our “kick off” party at Ink & Ivy in Greenville was therefore aimed at giving members the chance to put faces to names (or real faces to zoom square faces, at least) and trade feedback, experiences, connections, and support with each other and with the pitching companies.
And we were all in bed by 10 😊!
Day 2 – The State of VentureSouth
Over to downtown Greenville, to the ONE Building conference space courtesy of Roam.
A guiding principle at VentureSouth is that we always want our members to know what is going on, and why. This covers educational events, portfolio updates, deal term discussions, transparent diligence work, and much more – and to start the Summit Day 2 (after breakfast and coffee, of course) it covered providing our annual “State of VentureSouth” recap.
Wins celebrated, losses commiserated, portfolio performance analyzed, and more lessons learned from Matt D’s annual update. 2025 was a good year for VentureSouth; more capital returned to investors than deployed typically makes a good year, at least for some members…
With continued improvements to our cadence, reporting technology, and team coverage we think 2026 could be even better.
Day 2 – Practical Learnings about Exits
Angel investing is philanthropy until there are exits. In two panels we learned lessons from one (painfully) unsuccessful investment and two positive exits, Cadchat’s sale to GoEngineer and Zipit’s purchase by Wireless Logic. When, why and how to engage with bankers, how board members can lighten the load and focus the discussion, how creditors can become enemies and how debt can become deadly, and how to manage shorter-than-expected or longer-than-hoped investment horizons; all things to consider when planning for and executing entrepreneurial exits.
Day 3 – Sports Investing
Though not a deliberate theme, our lunch speakers provided differing-but-overlapping experiences of sports investing. Wallace Cheves, Greenville businessman and Chairman of Greenville Pro Soccer, outlined his experience – and introduced his current public fundraising, which you can learn more about – and, if you’re interested, indicate that interest to invest right here. Open rounds tally: +1
Day 3 – VentureSouth Meeting
To wrap things up, our annual “Member Migration” meeting – a VentureSouth meeting where our members “migrate” to access the content – filled the final afternoon. Content included:
- a new company pitch (Open rounds tally: +1)
- two “refresher” pitches from companies emerging from our diligence process and closing up open rounds (Open rounds tally: +2)
- three further “open rounds” of portfolio companies that hadn’t pitched yesterday (Open rounds tally: +3)
- two companies currently raising capital on the Vicinity platform (Open rounds tally: +2)
- a lightning round of deals “coming soon” to the Vicinity platform (Open rounds tally: +6)
- and a disturbing amount of step-climbing cardio to distribute the microphones for the poor host.
And of course there was swag, donuts, bourbon, boats, tough questions, last-minute agenda shuffles, the world’s most supportive mattress, Healthycell sample sachets, and all the fun joys of executing a 200-person 2-day conference!
That was the agenda. What were the highlights?
For Jewel: After months of working closely with our angels and founders through the diligence process, the Summit feels like a true full-circle moment! The conversations that start in data rooms and diligence calls come to life in person, and it’s energizing to see how much progress companies have made since we first evaluated them!
For Charlie: Once again, we were proud to deliver maple bacon donuts to the membership!
- And for Matt: It's hard to believe we've been hosting these annual summits for a decade, but sensing the energy, excitement and learning that comes from gathering our investors and founders never gets old. We're always impressed and invigorated by the work our companies are doing to solve big problems and create new opportunities - from medical breakthroughs to AI applications - but this year was the first time we had an electric boat parked in a downtown plaza, so that was a new one for the highlight reel!
If you came along, we would love to hear your highlights – and learn what we can do better so that the next 10 summits keep improving!
What now?
For those keeping count, there were 23 potential investment rounds (14 VentureSouth private deals and 9 Vicinity public deals) for consideration by members. If your complaint about angel investing is there aren’t enough deals to consider, we may know a group for you.
(If your complaint is there are too many to evaluate, we hear you; luckily there are plenty of supporting materials to review, and other methods like an index-fund approach to simplify selection.)
Having debriefed and decompressed, work resumes on our 2026 mission to do more to Make Money. Have Fun. Do Good.
We hope you will join us for the next year, and that you will join us at the 11th VentureSouth Summit in 2027 as part of your membership.