Chicago Ventures

Congrats! ?? CV portfolio company Aeropay announces $20M Series B. Read more in TechCrunch below, and please join us in congratulating CEO and Founder Daniel Muller on the company's progress!

?? ZenBusiness survey shows that 90% of small business owners anticipate AI becoming essential or frequently used in the near future... They're also cautious, particularly in customer service, tax filing, sales and business coaching. "AI is no longer a distant concept--it's becoming an everyday necessity for small business owners, and our research corroborates it," said Sameer Gulati, chief product officer at ZenBusiness "The challenge now isn't just making AI available--it's ensuring entrepreneurs can use it in ways that truly support the very specific needs of their business. At ZenBusiness, we are focused on building AI tools that are intuitive, effective, and, most importantly, designed with business owners' trust in mind." Full story ??

?? Say hello to Archie Chat ???? data.world's AI assistant is here to revolutionize how businesses interact with their data catalogs. ???: "Organizations today are drowning in data but starving for insights," said Brett A. Hurt, CEO and Co-founder of data.world. "Archie Chat transforms how teams interact with their data catalog, making knowledge discovery as simple as having a conversation." ???: "Data catalogs fail when people don't use them. Archie Chat changes that. It makes interacting with your data as easy as having a conversation, which means more people get the answers they need, faster. That's what drives real adoption," said Tim Gasper, Chief Product Officer at data.world. Full details ???

?? Congratulations to project44, named a leader in the 2025 Gartner Magic Quadrant for real-time transportation visibility platforms for 5th consecutive year ?? ??????? It's also the 3rd consecutive year that project44 been placed highest on "Ability to Execute" and furthest on "Completeness of Vision." "We feel this recognition reflects our decade-long commitment to deep customer partnerships and our focus on delivering business outcomes that truly matter. As we continue to pioneer hard ROI AI innovation to solve simple and complex supply chain challenges, we believe our leadership position in the industry will strengthen, creating even greater value for our customers," said project44 CEO and Founder Jett McCandless.

?? Aeropay expands its banking network, partnering with Regent Bank to bring improved payment flexibility and real-time transactions to their customers in Oklahoma and Missouri. "Businesses need banking partnerships that prioritize flexibility, reliability, and risk mitigation," said Steve Baker, Chief Innovation Officer at Regent Bank. "Working with Aeropay aligns with our mission to deliver secure, customer-centric payment solutions, empowering businesses to scale with confidence." "Aeropay's mission is to create a seamless and secure digital payment ecosystem for businesses, and our partnership with Regent Bank marks another step in achieving that goal," said Daniel Muller, Founder and CEO of Aeropay. "By adding Regent Bank to our network, we're providing our clients with enhanced access to modern payment services and a more resilient banking infrastructure." Details ??

?? This is great – project44's new partnership with SONAR helps shippers save 2-3% on full truckload freight ??????? Project44's real-time visibility + SONAR's high-frequency freight data = shippers can benchmark rates, negotiate better, and optimize procurement ?? "By integrating SONAR with project44 Freight Procurement Analytics, we're leveraging our carrier-agnostic platform to help our customers take their procurement strategies to the next level. This integration allows shippers to benchmark rates against live market conditions, uncover cost-saving opportunities and negotiate better contracts with confidence, generating significant cost reductions and an increase in on-time-in-full percentage by up to 20%," said project44 Founder & CEO Jett McCandless More info from @freightwaves' @grace sharkey ???https://bit.ly/4kt1uQM

Another great read from OneRail’s Bill Catania – Bill breaks down exceptions management, "the catch-all term for handling (or managing) anything that goes wrong in the logistics process" ?? Recommended! #LastMileDelivery #LogisticsTech

??? What's next for voice tech? Telnyx has 2025's top trends in telephony ?? 1. AI improves operational efficiency and drives actionable insights 2. Contact center automation will redefine customer experiences 3. Edge computing enables low-latency, scalable communications Click through for the full list with detail... ?? https://bit.ly/4gZf1wH

Haven't checked out G2's #BestSoftware2025 ?? yet? We obviously think the highlight of this year's list is the new addition of our portfolio co project44 ?? And this year's list is all about #AI – "always included" ?? "In the words of [G2] VP of Research Insights Tim Sanders, "AI now stands for Always Included, and you can see this throughout our list of winners. To compete in this age, software vendors need to leverage the power of AI to maintain their edge." For more, G2 has a great deep dive into the US and Global winners ??

?? Got an #AI project you think might be something big? Telnyx's new AI Accelerator gives startups $20K in free credits to power next-gen applications. Details: "The program supports startups building AI-driven VoIP applications, communication tools, call centers, IOT apps and real-time WebRTC solutions. Participants will receive exclusive discounts, priority support, and full access to Telnyx's AI voice, WebRTC SDKs, and Flow automation tools." Apply now at the link... ??