Drew's News
Vol: 10
January 6, 2026
Greetings from Chattanooga - I’m back and with a few personal notes. In full transparency, it was a difficult end of 2025. I lost my dad a few weeks ago after a lengthy cancer battle. He was a third generation entrepreneur and inspirational in more ways than I can articulate. He modeled a life of kindness and service, and I will forever be grateful for his impact on me, and my family. In addition, after many, many hours of diligence (and sunken costs), our small business acquisition fell through only a few days before close. I can’t go into too much detail on this one for contractural reasons, but it was our call (and the right decision). I’ll say this: Good representation is critical in these type of transactions, and our recent experience exposed a fundamental gap between main street business acquirers and underprepared sellers. One of my goals in 2026 is to address this pain point. If you’re interested in buying (or selling) a business, I’ve got a few resources I’m happy to share with you. Despite the setbacks, I'm committed to connecting and cultivating our Chattanooga entrepreneurial ecosystem, now more than ever. Onward! Drew |
Connections + Congrats Chattanooga Founders Forum recently hosted Brian Trautschold, who shared his journey co-founding Ambition, including the pivot that changed their trajectory, their acceptance into YC, and scaling from small business to enterprise clients. Thanks as always to Jay Shaffer and Jake Fishman for organizing these events. Morgan Holl and Overlooked Materials continues to make noise with their partnership pilot program with the City of Chattanooga. The program aims to recycle glass locally, and they've added 3 new zones in 2026. Click here to see if you live in the pilot area to help Morgan and his team. According to the Congress of New Urbanism, Chattanooga has steadily improved by sticking to a long-term vision focused on walkable neighborhoods, strong public spaces, and smart growth. Consistent collaboration between civic groups, nonprofits, and private developers has helped the city grow without losing its character. Note the Westside arial illustrations, which I personally hadn't seen before. Shappi, a travel-tech startup co-founded by Ecuadorian Karla Valdivieso and based in Chattanooga, recently acquired the Chilean platform Comparto mi maleta, combining their technologies, users, and operations as part of a $34 million business move. The merged companies plan to operate across Ecuador, Colombia, Chile, and Peru next year under Shappi’s model to grow revenue and scale their travel logistics services. Shappi has investment from Brickyard. Another Brickyard-backed company was recently profiled by Teknovation. Electrokare is a Chattanooga-based health-tech startup that uses AI and ECG signals from wearables to give athletes deeper insights into hydration, electrolyte balance, and performance readiness beyond what typical fitness trackers show. Founder Mitchell Leshchiner built the platform through accelerator programs and a waitlist of more than 35,000 users. |
Connections + Coffee Help me fulfill my 2026 goal of having coffee six times a month with entrepreneurs and the startup supporters who make it all happen. Book here: LINK |
Connections + Capital
TVFCU Idea Leap Loans and Grants- LINK
Applications open - TVFCU's Idea Leap initiative is distributing $225,000 in grants of up to $30,000 each to qualified small businesses. Eligibility requirements include: 2-25 employees (owner included), maximum annual revenue of $2.5 million, at least 12 months of operational history with proven revenue generation, and location within TVFCU's 17-county service area.
InvestTN Regional Seed Fund - LINK
This is a $28M Tennessee-focused initiative investing in startups served by 7 Regional Entrepreneur Centers across all 95 counties. Investments range from $25,000 to $250,000.
Small Business Innovation Research Program - LINK
Transform your innovations into market-ready solutions with the SBIR Program. This strategic federal funding initiative empowers small businesses to commercialize cutting-edge research and technology. Whether you're developing next-generation solutions or pioneering scientific breakthroughs, SBIR provides the capital and resources to accelerate your journey from concept to commercialization.
Morgan Stanley Inclusive & Sustainable Ventures - LINK
Morgan Stanley provide early-stage innovators with access to capital and resources to help them develop and scale. The mission is to foster a more equitable and sustainable investment landscape.
Connections + Events
Lunch + Learn at The Arena: Outgrowing Old Paradigms with Brandon Clift (LINK), Friday, January 9, 12pm to 1pm, 1271 Market St. B, Chattanooga, TN
Venture South's Angel Investing 101 with Paul Clark, Thursday, January 29th, time and location TBD. Open to Public.
Chattanooga Founders Forum, January 22, 12pm. Meet with like-minded folks who want to drive the Chattanooga startup ecosystem.
Have an event? Reply to this email.
Personal Notes We spent Christmas skiing in Idaho this year. We were grateful for the snow, which is more than I can say about our friends in Utah and Colorado. |
Footnotes My mission is to cultivate the startup community through connection. I'm a big believer in building this newsletter in public, so if you have ideas on how to further this ecosystem initiative, reply back to this email and let's work on this together. This community is made up of small business owners, investment bankers, organizers, investors and economic development leaders who all share a belief that a rising tide lifts all boats. Share this email to someone who will provide value to this community. We are (slowly) building a database for Chattanooga that will be published soon for free. Have you submitted your startup? Help me build this community resource here. I'm also building a curated database of businesses for sale. More later. |