Zaid Rahman

He grew up in Dubai and comes from a family of construction entrepreneurs.⁠[1][2]

On the Around The Coin podcast in 2024 he said that he comes from an Indian family that runs several small businesses, including a construction business and a small logistics business, and recalled his father asking “how much cash should we bring to the table today.” THE BRIDGE wrote in 2025 that he is from India and that, because his family ran a construction business, he saw the cash-flow problems of mid-sized companies at close hand.⁠[3][4]

The Around The Coin episode notes state that he previously founded two startups, Pilot Labs and Volley, and that he exited his first startup at 19. TechCrunchTechCrunchTechCrunch is an American technology news outlet founded in 2005 by Michael Arrington and Keith Teare and headquartered in San Francisco; it mainly covers technology companies, startups, and venture capital, and hosts events such as TechCrunch Disrupt. Its ownership passed successively through AOL, Verizon, and Yahoo, and in 2025 Regent announced its acquisition.Open the full entry wrote in 2016 that he had run Pilot Labs, an instructional technology consultancy in Dubai.⁠[3][5]

On the Around The Coin podcast he said that Volley began in 2015 as an effort to build a tool to “teach computers how to understand knowledge,” and that the company was “almost a decade ahead of its time.” TechCrunch wrote in March 2016 that Volley had spent about a year in stealth developing its first learning product.⁠[3][5]

On March 10, 2016 EdSurge wrote that Volley Labs, a San Francisco company describing itself as a “learning technology” startup, had raised a $2.3 million seed round from investors including Reach Capital, Zuckerberg Education Ventures and TAL Education Group, along with angel investors from AppleAppleApple is a public technology company founded in 1976 and headquartered in Cupertino, California, United States. Its business includes the iPhone, Mac, iPad, wearables, and services such as digital content, payments, and cloud storage. The company builds its product system through in-house hardware, operating systems, and services.Open the full entry, Blackboard, Dropbox and Udemy; the article names him as co-founder and CEO and the other co-founder Carson Kahn as product and technical director. TechCrunch wrote the same day that the round was led by Reach Capital and that Zuckerberg Education Ventures is the investment vehicle of Mark ZuckerbergMark ZuckerbergMark Zuckerberg is the founder of Facebook, Chairman and CEO of Meta, and a co-founder of the Chan Zuckerberg Initiative. His work spans social networking, virtual reality, and artificial intelligence.Open the full entry and Priscilla ChanPriscilla ChanPriscilla Chan is a physician trained in pediatrics who co-founded the philanthropic and scientific organization Chan Zuckerberg Initiative with Mark Zuckerberg and serves as its co-CEO.Open the full entry.⁠[6][5]

EdSurge wrote that Volley’s founding team had five people; Carson Kahn said the team wanted a “magic lens through which we could learn anything”; the team first explored peer-to-peer learning and then settled on supplementing textbooks with curated web content at the moment a student is confused; the product was aimed mainly at students in advanced high school and college courses: a student scans a textbook passage with a smartphone and Volley returns “cards” explaining terms and difficult passages, each with an estimated reading time, which students can save as favorites; the favorites list can become a study guide that a student could use or share. He said the goal was to make learning feel “automagical.”⁠[6]

TechCrunch described Volley as a learning-assistant camera app: a student photographs a textbook page or homework problem and, using machine learning and natural language processing, the app returns within seconds explanations of key facts, tricky parts and prerequisites, with links to parts of Khan Academy courses, WikipediaWikipediaWikipedia is a free, multilingual online encyclopedia launched on January 15, 2001, written collaboratively by volunteers around the world and hosted by the nonprofit Wikimedia Foundation; it is one of the most visited websites in the world.Open the full entry articles and reference PDFs uploaded by teachers; its “Concept Graph” identifies what a student must understand first, and Carson Kahn gave the example that understanding photosynthesis requires understanding glycolysis. The article states that the product was then in private alpha and that the company planned to keep it free for students and to charge textbook publishers, education service providers and school networks.⁠[5]

TechCrunch listed the core team as CEO Zaid Rahman; Carson Kahn, former CEO of Keystone Learning Systems; Ryan Orbuch, founder of the Apple Design Award-winning productivity app Finish; and Adam Ashwal, developer of the machine-learning plugin Liaison Vision. The article states that several of them took untraditional paths through education, Orbuch having sidestepped college to found Finish.⁠[5]

EdSurge wrote that he and Carson Kahn described their work as “trying to computationally understand the world's knowledge,” and declined to give many details of their algorithms because they hoped to apply for patents; the team aimed to have “alpha technology” for students to test by summer 2016, and the co-founders named Wolfram Alpha among organizations doing comparable work.⁠[6]

On June 16, 2017 the Thiel Foundation named the 25 members of the 2017 class of Thiel Fellows, and he was among them. The announcement states that the two-year Thiel FellowshipThiel FellowshipThe Thiel Fellowship is a two-year grant program started by investor Peter Thiel and run by the Thiel Foundation that funds young people who skip or stop out of college to build new things instead. The program has been criticized by figures in education for encouraging young people to leave college.Open the full entry provides $100,000 and mentorship from the Thiel Foundation’s network of technology entrepreneurs, investors and scientists, and encourages fellows to pursue full-time entrepreneurship instead of going to college; Jack Abraham, executive director of the Thiel Fellowship, says in the announcement that the fellows were selected from thousands of applications received from around the world. The list gives him as from Dubai, United Arab Emirates / San Francisco, CaliforniaCaliforniaCalifornia is a U.S. state on the Pacific coast; its capital is Sacramento and its largest city is Los Angeles. California was admitted to the Union on September 9, 1850, as the 31st state. Its population at the 2020 Census (April 1, 2020) was 39,538,223, the largest of any state.Open the full entry, with the project Volley in the field “Artificial Intelligence,” and describes him: “Zaid is CEO of Volley, an artificial intelligence company focused on personalizing enterprise learning.”⁠[7][7]

Refresh Miami described him in 2021 and 2025 as a Thiel Fellow and serial entrepreneur, and THE BRIDGE described him in 2025 as a serial entrepreneur who came out of the Thiel Fellowship. On the Around The Coin podcast in 2024 he said that he was lucky to be part of the Thiel Fellowship and joked that he is “the least successful amongst them”; he said the fellowship provided $100,000, and said that “you don't really need a formal education to go attack very big ideas.”⁠[8][9][4][3]

Technology Magazine wrote on May 17, 2020 that JPMorgan ChaseJPMorgan Chase & Co.JPMorgan Chase & Co. is a financial holding company headquartered in New York that operates investment banking, consumer and small business financial services, commercial banking, financial transaction processing and asset management under its J.P. Morgan and Chase brands; its roots trace back to the Manhattan Company of 1799.Open the full entry had invested in Volley, without giving an amount. The article describes Volley as using artificial intelligence to create customized training programs for enterprise employees, cutting training costs by up to 50% and largely targeting Fortune 500 firms; it names Carson Kahn as Volley’s founder and CTO and Paul Walker, former global co-head of technology at Goldman SachsGoldman SachsGoldman Sachs is an American financial services group headquartered in New York whose businesses include investment banking, securities trading, asset management, and wealth management. It traces its origins to the commercial paper business Marcus Goldman founded in 1869; it listed on the New York Stock Exchange in 1999 under the ticker GS and became a bank holding company in 2008. David Solomon serves as chairman and chief executive officer.Open the full entry, as a senior advisor, and states that Volley’s existing investors include current and former executives of Goldman Sachs, Apple, Facebook and Dropbox.⁠[10]

On the Around The Coin podcast in 2024 he said that one specialized area in which Volley had a lot of success was “cyber education,” that “JP Morgan was our biggest customer and then they became our biggest investor,” and that “ultimately that company wasn't a huge slam dunk success story” because the timing was a little off. THE BRIDGE wrote in 2025 that JPMorgan Chase had made a strategic investment in Volley and that Zuckerberg Education Ventures had also invested.⁠[3][4]

In October 2020 he left Silicon Valley for Miami. Refresh Miami wrote in May 2021 that the partners of 305 Ventures had moved to Miami from California or New York, and that after he arrived in October he and Joey LevyJoey LevyJoey Levy is an entrepreneur in sports betting and fantasy sports who co-founded the micro-betting and media company Betr with Jake Paul in 2022 and serves as its chief executive; he had earlier co-founded the daily fantasy sports site Draftpot while a student at Columbia University, was named a Thiel Fellow in the 2016 class of the Thiel Fellowship, and co-founded the sports-betting technology company Simplebet in 2018.Open the full entry set up a group, The305, which held small dinners and networking events and quickly grew to more than 1,000 people.⁠[1][11]

In October 2020 he and Hadi Solh, a former McKinseyMcKinsey & CompanyMcKinsey & Company is a management consulting firm headquartered in New York, United States. It was founded in Chicago in 1926 by University of Chicago professor James O. McKinsey and, after Marvin Bower established its “professional service” principles, grew into one of the largest pure consulting firms in the world; as of October 2026 it has more than 100 offices in over 50 countries and about 40,000 employees. It has also repeatedly faced regulatory investigations and public criticism over episodes such as its work with Enron, a former leader’s insider trading case, and its consulting for opioid manufacturers.Open the full entry and Goldman Sachs executive, launched Flexbase, an automated payment platform for contractors and the construction industry; he said, “We knew how much money construction companies make.” Refresh Miami wrote in 2023 that the company first focused on construction largely because much of his family works in that field, and that he later saw financial management problems across all small and mid-sized business sectors.⁠[8][2]

On May 16, 2021 Refresh Miami profiled the new fund 305 Ventures, an early-stage fund run by founders who invest in other founders with a presence in Miami; its partners were Rahman, Joey Levy, Kingsley Advani and Michael Melikian. The article describes him as founder and CEO of Flexbase, then a proptech company based in Miami, and as an angel investor in 23 companies. It states that the fund planned to invest in 40 companies through its $5 million fund, writing checks of $25,000 to $100,000; that it had invested in 10 startups over the previous few months, with three more fundings in final stages; that a second fund, possibly with larger checks, was already being planned; and that it had partnered with Florida Funders to find promising South FloridaFloridaFlorida is a U.S. state occupying mainly the Florida peninsula, with its capital at Tallahassee; its most populous city is Jacksonville. It entered the Union on March 3, 1845, as the 27th state, and had a population of 21,538,187 in the 2020 census (April 1, 2020).Open the full entry startups, Florida Funders also having invested in 305 Ventures as a limited partner.⁠[11]

On the Around The Coin podcast in 2024 he said that he and Joey Levy got together first and later recruited Michael Melikian as a full-time partner; he said they would rather call themselves “angel investors rather than full time VCs,” writing small checks that grew into a small fund. The host introduced him on the show as a founding and managing director of 305 Ventures, and the episode notes state that he co-founded it; Refresh Miami called him in 2023 a founding partner of the Miami-based early-stage venture fund. The 305 Ventures website describes it as an early-stage VC fund run by active founders investing in other founders and lists portfolio companies including Betr and Flex.⁠[3][2][12]

Refresh Miami wrote on May 18, 2021 that Flexbase had raised a $2.5 million pre-seed round from investors including Suffolk Technologies, Hustle Fund, Romulus Capital, Banana Capital, Great Oaks Venture Capital and the angel investor Sriram Krishnan, and named him as Flexbase’s co-founder and CEO. The article states that bills of the roughly 10 million construction contractors in the United StatesUnited StatesThe United States is a federal country in North America made up of 50 states, the District of Columbia as the seat of government, and territories such as Puerto Rico and Guam; its capital is Washington, D.C. The Continental Congress adopted the Declaration of Independence on July 4, 1776. The 2020 census (April 1, 2020) counted a resident population of 331,449,281, and the 435 seats of the House of Representatives are apportioned among the states on the basis of the census.Open the full entry typically go unreconciled for at least 100 days, that Flexbase aimed to “break the cycle of borrowed cash flow,” and that the platform connected to more than 85 lenders and offered one-click working capital.⁠[8]

On November 11, 2021 Refresh Miami covered the Flexbase Card, a new credit card from the Miami-based Flexbase. He said, “At Flexbase, our thesis is that most construction companies are either completely broke or one step away from being broke.” He said, “The average time to get paid is about 100 days. But with Flexbase payments, our goal is to bring that down 50 days”; he said banks “don't know how to underwrite construction companies,” that businesses using the Flexbase Card “don't need to rely on short term loan sharks,” that the company underwrote using a combination of tools including analysis of a business’s inflows and outflows, and that the card’s receipt and project-tagging features could save dozens of hours of reconciliation work.⁠[1]

The article states that Flexbase then had 16 employees, with a team already in Miami, and was recruiting in South Florida, mainly for sales and marketing, to support expected growth of two to three times over the following quarters; he praised Miami’s quality of life, weather and diversity. The article also states that he runs 305 Ventures, an early-stage fund that invests nationwide with a focus on Miami.⁠[1]

TechCrunch wrote in 2025 that he formed Flex in 2022, evolving it from Flexbase Technologies, a construction platform; Refresh Miami wrote in 2025 that the company pivoted to financial services in 2022. The company description in a Flex release on Business Wire states that it was founded in 2022, and the company timeline on Flex’s website lists for 2022 the “First Flex card swipe” and “Hired first 5 employees.” The website footer names the legal entity as Flexbase Technologies, Inc. Refresh Miami wrote in 2023, by contrast, that he co-founded Flex with Hadi Solh in 2020 and that the company was formerly known as Flexbase.⁠[13][9][14][15][16][2]

On June 6, 2023 The #MiamiTech Pod published a 38-minute-54-second episode with him as guest. The episode notes describe him as founder and CEO of Flexbase and list as topics who he is, “Dropping Out Of College For The Thiel Fellowship,” working in AI before it was popular, building a finance super app, investing with 305 Ventures, his biggest lessons as a founder, and culture shock in Miami.⁠[17]

Refresh Miami wrote on September 19, 2023 that Flex had raised a $20 million Series A equity round led by Florida Funders, with Home DepotThe Home DepotThe Home Depot, Inc. is an American home improvement retailer, the world’s largest by net sales for fiscal 2025, headquartered in Atlanta, Georgia.Open the full entry Ventures, MS&AD Ventures and Companyon Ventures participating, and $100 million in debt financing led by CIM to fund its credit card business. Flex’s flagship product was a credit card with net-60 payment terms, and the company aimed to become a platform covering back-office finance including expense tracking, banking and treasury management; it had served more than 25,000 small businesses. TechCrunch wrote in 2025 that Flex came out of stealth in September 2023 with a business credit card and expense-tracking product.⁠[2][13]

He said he founded Flex to address two problems: that “there are just too many tools in B2B finance,” with most small and mid-sized businesses lacking a CFO so that owners keep their finances “in their head or in Excel”; and that such businesses often lack the working capital to keep operating. He said, “We are enabling business owners to achieve the American dream.” He said the equity round would fund product development and the hiring of marketing and sales staff. Saxon Baum, general partner of Florida Funders, said, “Zaid is a once-in-a-lifetime founder: a Thiel Fellow, and someone who’s building things in the right way.”⁠[2]

On March 13, 2024 the Around The Coin podcast published host Stephen Sargeant’s interview with him (episode 503). The episode notes describe him as founder and CEO of Flex and quote Flex’s description of itself as “the B2B fintech company taking the complexity out of credit and finance management.”⁠[18][3]

In the episode he said that Flex is his third company and that it then had 43 people; he said the common denominator he saw across his family’s businesses was that “finance sucks,” discussed the two problems Flex addresses, back-office complexity and lack of working capital, and named capital-intensive industries such as construction, logistics, trucking and e-commerce. He also said the company “had to actually switch off our paid advertising” in the fourth quarter, and said, “I don't really believe in work life balance.”⁠[3]

TechCrunch wrote on March 5, 2025 that Flex had raised $25 million in equity at a valuation of “just under $250 million,” led by Titanium Ventures with Companyon Ventures, Florida Funders, MS&AD Ventures, AAF Management and First Look Partners participating, and that Victory Park Capital had provided a $200 million credit facility used exclusively for the credit card business. That brought Flex’s totals to $45 million in equity and $300 million in credit facilities, and Yash Patel, general partner at Titanium Ventures, joined the board. Refresh Miami described Flex the next day as a Miami/New York startup with thousands of business customers.⁠[13][9]

TechCrunch wrote that Flex passed $1 billion in annualized total payment volume about 18 months after launching its card and bill-pay automation product and was growing 25% month over month; he expected revenue to grow fivefold in 2025 but declined to disclose revenue figures. Flex’s average customer earned about $25 million in annual revenue, and its customers included the logistics company Shoreside Support, the men’s grooming brand Freebird and the construction company MOD Partners; he said many customers had switched from the American ExpressAmerican ExpressAmerican Express Company is a payments company headquartered in New York that issues credit and charge cards and operates its own payments network; founded in 1850, it is listed on the New York Stock Exchange.Open the full entry Centurion (“Black”) Card. The company had 64 employees at the end of 2024, up from 28 a year earlier, and planned to use the new money partly to build AI and B2B payments teams in New York and San Francisco.⁠[13]

He compared Flex with the fintech companies Ramp and Brex but said Flex focuses on mid-market business owners who are also the CEOs of their companies, rather than on enterprises or venture-backed startups; he called Flex “a financial co-pilot” said that business owners tend to “co-mingle their personal and business expenses,” and said, “All business entities and personal life sit in a single dashboard.”⁠[13][9]

On December 4, 2025 Flex announced on its website a $60 million Series B equity round led by Portage, with participation from Titanium Ventures, Wellington, Crosslink Capital, Companyon Ventures, Spice Expedition, Florida Funders, FirstLook Partners, MS&AD Ventures, Restive and others, bringing its total equity raised to $105 million; the announcement states that revenue had grown fourfold over the previous year and private credit offerings had tripled, groups its products into five areas (private credit, business finance, personal finance, payments and ERP), and gives the company’s address in Miami, Florida. It is signed “Zaid Rahman, CEO & Founder,” and in it he says, “Middle-market business owners employ 40% of Americans, but the financial system has never been designed around their complex needs.”⁠[19]

Refresh Miami described Flex the same day as a Miami-born startup positioning itself as an AI-native private bank for high-net-worth business owners, and wrote that the round was led by Portage with Florida Funders participating. The article states that he described the middle market, profitable companies with $3 million to $100 million in revenue, as the financial backbone of the country, and that in talking to these owners he kept hearing, “No one has ever built a system for people like us.” He said, “Flex is the first platform that supports every step of their financial lives.” THE BRIDGE wrote on December 24, 2025 that, in the company’s figures, Flex’s revenue had grown fourfold in 12 months and its annual payment volume had risen from $1 billion to $3 billion, with customers using more than four products on average; its list of investors in the round also includes Tusk Venture Partners.⁠[20][4]

American Banker wrote on July 14, 2026 that Flex, a fintech that helps high-net-worth business owners manage personal and business cash flow in one place, had raised another $70 million at a valuation the article gives as $1.2 billion (a figure the page summary attributes to the company itself), more than double its valuation six months earlier; Flex had raised $180 million in equity and $300 million in debt in total and was launching a global banking service built on stablecoin payments for cross-border settlement. A photo caption names him as Flex’s founder and CEO. Rudy Yang of PitchBookPitchBookPitchBook is a private capital market data, research and software company headquartered in Seattle, Washington, United States. Founded by John Gabbert in 2007, it was fully acquired by Morningstar in 2016 at a valuation of $225 million and operates as a Morningstar subsidiary. The PitchBook segment’s revenue was $671.8 million in 2025.Open the full entry calls stablecoin adoption in global business banking “inevitable” in the article.⁠[21]

A Flex release on Business Wire, datelined New York, announced the Flex Visa Infinite Business Credit Card, stating that it made Flex the first U.S. fintech in its category to introduce a Visa Infinite Business-branded credit card and that the card replaced Flex’s previous commercial MastercardMastercardMastercard Incorporated is a technology company in the global payments industry whose principal operating subsidiary was formed in November 1966. It is headquartered in Purchase, New York.Open the full entry product. As Flex’s founder and CEO he said, “We're proud to bring our customers a business card that's as sophisticated and flexible as they are.” The release describes Flex as “the B2B fintech company redefining financial management for business owners,” offering a business credit card, Flex Banking and several back-office tools.⁠[14]

The company timeline on Flex’s website lists for 2023 the launch of the Flex Credit Card, $1 million in transactions, the acquisition of Ghost Financial and $120 million raised in debt and equity; for 2024 the launch of Flex Banking, global payments and B2B payments, and more than 10,000 attendees at Flex-hosted events; and for 2025 $1 billion in transactions and the launch of bill pay (accounts-payable automation). The website’s homepage presents Flex as “Private Banking For Business Owners.”⁠[15][16]

Thiel Fellowship: Official website: https://thielfellowship.org/ (opens in a new window).⁠[22]

Flex: Official website: https://www.flex.one/ (opens in a new window).⁠[16]

305 Ventures: Official website: https://www.305.ventures/ (opens in a new window).⁠[12]