VC @ Wellington | co-founder @blckventureinst | @KauffmanFellows class 25 | ex @Stanford athlete | tech+investing+culture | my thoughts are my own

Joined August 2020
Jackson Cummings retweeted
Today we released v1.7.2! github.com/TraceMachina/nati… 6 months since v1.0.0 we have hundreds of companies using NativeLink across a variety of industries and nearly 80 contributors. We also have grown enterprise users by >=700% YoY. 🤯 ty ty @sharpshoot for everything!
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Jackson Cummings retweeted
Today, we're opening Flex Elite to the public. The personal credit card from Flex (@flexsuperapp). Invite only. Built for high spenders. Up to 5% cashback on everything*, no annual fee. More than two years in the making. Members get: > Up to 5% cashback on every category* > 24/7 travel concierge > Top hotels through our own partner network: Aman, Dorchester Collection, Rosewood, Eden Rock St Barths and more > Flights, private jets, villas, yachts with our travel advisory team > VIP access to Flex-curated experiences: Monaco F1, Art Basel, the Super Bowl and more > Personal and business finances in one dashboard, one login Founders who run their personal and business finances through Flex get the highest rewards tier in the industry. Request your invite: flex.one/elite
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Jackson Cummings retweeted
Today, Stablecoin Wallet & Payments are rolling out on @FlexSuperApp. Our early customers are already transacting billions in annualized volume with us.  No more juggling multiple platforms for your fiat and stablecoin operations. You can now hold, send, receive, convert, and spend stablecoins directly through Flex in a 170 countries: > seamless on/off ramps > settlement in seconds > USDC & USDT  > best in class banking with > all popular chains > available 24/7/365 > private banking support  > on-chain credit globally > global visa cards (coming in Q4) If your business runs on both fiat and stablecoins, bring it all under one roof with Flex. Request access to be in the first group.
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Jackson Cummings retweeted
Day 1. Barely scratched the surface of our multi decade vision.
another insane month at @FlexSuperApp. we’re consistently hitting $500k revenue days and adding seven figures in new ARR every week. demand is growing so quickly that our onboarding team physically can’t keep up with the volume of applications. we’ve never had this much revenue, profit, cash on hand, and brand momentum. the craziest part is that we’re still launching six more products before the end of the year, all designed to expand our banking suite: > stablecoin payments > flex elite (5% cash back on personal spend) > flex travel & points program > payment processing paired with our existing suite of: > flex net 60 credit cards > reward cards > business banking > AP/AR > AI CFO the vision is much bigger than building another business bank: we’re building one financial home where founders can manage both their business and personal finances. the next four months are going to be absolutely insane.
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Jackson Cummings retweeted
Proud to share Flex has 4x'd its annualized total payment volume (TPV) since the end of 2025, adding $10B in just a quarter. Grateful for our team's ambition and velocity! We are hiring. Come join one of the most cracked teams in all of tech today.
We hit a new milestone at @FlexSuperApp: $20 billion in annualized payment volume. We ended 2025 at $5B, reached $10B just four months later, and have already doubled again to $20B. We’re incredibly grateful to our customers for continuing to trust Flex and making this growth possible. On to $50B, then $100B, then $1T.
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Jackson Cummings retweeted
🚨 BIG NEWS 🚨 PHYND is officially live on LG in the U.S.! Whether you're racing, solving puzzles, or playing with the family, your next favorite game is just a few clicks away—and it's completely free. Search "PHYND" on your LG Smart TV (2021+) and start playing today. 🎮 No console. No downloads. No subscriptions. Read more: phynd.co/phynd-expands-free-… @LGGamingGlobal #LGTV #CloudGaming #PHYND #Playfree
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Jackson Cummings retweeted
We conquered the US over the last 3 years. Flex grew to a $1.2B+ valuation and $10B+ in annualized payment volume. Today, we’re bringing that same experience to businesses all around the world. Introducing Flex Global: 170+ countries 32 currencies 2% cashback 24 products
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Jackson Cummings retweeted
Today, @FlexSuperApp, raised $70M Series B1 to launch The Full Financial Home for Business Owners. Making Flex officially a unicorn. Led by @RyanQualtrics and @ryanjsweeney’s @halo_fund, with participation from existing investors. And we're introducing Flex Global.
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Jackson Cummings retweeted
If you're affected by Parker Cards, @FlexSuperApp is here to help. - Net60 credit cards - Highest rewards - Working capital (12 months) - Support new businesses to multi-billion dollar companies - Global banking, available in 170 countries* - 32 currencies (EUR, RMB, INR, etc)
*PARKER CARD CEASES OPERATIONS Parker, the YC19 fintech that served ecommerce merchants with credit cards, has officially ceased operations on May 4th '26 Patriot Bank, parkers banking operations partner, issued an official statement to clients confirming Parker raised >$200m
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Jackson Cummings retweeted
Proud to see Flex listed by Fast Company’s Most Innovative Companies in 2026 list with great company like Nvidia, Anthropic, Robinhood, Bilt, Plaid, and Circle. Day 1. @FlexSuperApp
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Jackson Cummings retweeted
Flex is growing unbelievably fast. Now at $6.5B in Total Payment Volume (TPV) in <2.5 years. Growing 20%+ MoM. Fuel your ambition: flex.one
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Jackson Cummings retweeted
Silicon Valley forgot to build for the middle market, the 350K HNW business owners employing 40% of America’s payroll. Today, we’re fixing that. @FlexSuperApp's $60M Series B equity round led by @portageinvest, building the "AI-Native Private Bank" for HNW owners.
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Jackson Cummings retweeted
Yesterday we finished cohort 7 of @BlckVentureInst & I can honestly say, the cohorts just get more impressive. Cheers to you Cohort 7! Can't wait to see what you do! Big love to all our #BVIFam for always bringing it. ❤️❤️@RobertGordonIV #BVI4Life
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Happening Now: Our co-founder @Syd_Lykes leading a #LEGENDARY session with @chudson of @PrecursorVC for one of today's #BlackVentureInstitute sessions for Cohort 6! #BLCKVC #BlackVenture
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1. This panel with @4ocho, @julian_eison, @JacksonTheVC is soooo GOOD! Exploring the landscape of athletes' participation in VC & strategies, challenges, and opportunities they encounter. 2. Love that our #BlackVentureInstitute Panels are all #BVI alums! #VentureCapital #BLCKVC
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🎉 Exciting times at @BLCKVC as we kick off Cohort 6 of the #BlackVentureInstitute! Filled with immense joy and pride, witnessing a new group destined to redefine Black-led investments. Here’s to their journey ahead! #BVI #Cohort6 #FutureOfVC #Day2 #DiversityAndInclusion ✊🏾
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Back at it with our next cohort of @BlckVentureInst!! Welcome Cohort 6!! Incredible group of leaders 🔥 🚀 #BVIFam
Oh my word, @BlckVentureInst cohort 6 begins today and the epic journey of our #BVIFam continues. #BVI4Life
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Jackson Cummings retweeted
I’ve had the honor of watching @JacksonTheVC build this platform from Day Zero. My pride in him @frederikg191 @SashaMac17 & @LaVandezJones knows no bounds! CONGRATS on the $150M WAV Fund 1 close 🙌🏽 Thx @alexrkonrad + @Wellington_Mgmt + @KauffmanFellows forbes.com/sites/alexkonrad/…
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What an incredible moment - I remember @JacksonTheVC manifesting this (my brother - I'm so proud of you!) - AND what a team he has alongside him - @frederikg191, @SashaMac17, and @LaVandezJones! @Wellington_Mgmt WAV $150M Fund 1 in the books! Great article @alexrkonrad
Excited to announce Wellington Access Ventures (WAV), our first early stage venture fund at Wellington Management!! To learn more, read the full exclusive from @forbes about our $150M final close forbes.com/sites/alexkonrad/…
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Jackson Cummings retweeted
WAV's $150M fund comes as $$ for emerging managers and Black founders has mostly dried up. @DominicMadori recently wrote that 0.13% of U.S. venture dollars went to Black founders in Q3, which rounds to zero. Wellington's partnership contributed $50M to WAV, a show of support.
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