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Jason Caudill

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This article is about the American annuity industry executive. For other people of the same name, see the note under See also.

Jason Todd Caudill (known professionally as Jason Caudill, MBA) is an American annuity industry executive and entrepreneur, the founder of My Annuity Store, Inc., an independent, direct-to-consumer annuity marketplace incorporated in Fishers, Indiana, in January 2020.[1][2][3] Before founding the company he spent more than fifteen years on the distribution side of the annuity business, including wholesaling roles at Ash Brokerage and Raymond James, and he reports having personally placed more than $1 billion in annuity premium over his career.[1][4][11]

Under Caudill the company was named Top Multi-Carrier Annuity Platform by Insurance Business Review in 2025 and again in 2026, in both cases on the basis of an interview with him.[9][10][11] He hosts the My Annuity Store Podcast, launched in 2025, publishes an annual Deferred Annuity Buyer's Guide, and in 2026 launched Andy Annuity, an AI research assistant for annuity shoppers, and Annuity Journal, an annuity news publication.[14][21][23][25] The company's rate data and research have been cited by ThinkAdvisor, TheStreet and Wikipedia.[16][17][19]

Early life and education [edit]

Caudill earned a Bachelor of Science in Business Administration and Computer Information Systems from Ferris State University in Michigan, which he attended from 2000 to 2004, and a Master of Business Administration in entrepreneurship from Ball State University in Muncie, Indiana, graduating cum laude in 2005 after a year as a graduate assistant.[4][7] While in graduate school he interned with New York Life, where he obtained his first insurance license; the company's press page describes his background as "including time at Raymond James and New York Life."[8] His full name appears as Jason Todd Caudill on his FINRA BrokerCheck record.[1]

Career [edit]

Annuity distribution (2005–2021)

Caudill's early career was on the carrier and wholesale side of the annuity business. After an internship with New York Life in 2005, he was vice president of marketing at Standard Life Insurance Company of Indiana from 2007 to 2009.[4][8] From May 2009 to March 2017 he was regional vice president at Ash Brokerage in Fort Wayne, Indiana, a brokerage general agency that his biography describes as one of the largest in the country.[1][4] Over part of the same period, from 2013 to 2017, he was a registered representative of Mercap Securities, and he passed the Series 6 and Series 63 examinations in 2013.[1]

In June 2017 he became regional marketing director for the Midwest at Producers Choice Network, and he continued in that role at Raymond James after Raymond James acquired the network, until July 2021.[4] His FINRA record lists him as a registered associate of Raymond James & Associates, based in Fishers, Indiana, through July 2021.[1] His BrokerCheck record shows no disclosure events, and he has not been registered as a broker since leaving Raymond James.[1]

My Annuity Store (2020–present)

My Annuity Store, Inc. was incorporated in Indiana on January 7, 2020, with its principal office in Fishers.[2][3] The state filing lists Kiara Caudill, Jason's wife, as incorporator and president; the company explains that Jason's securities licenses and his position at Raymond James prevented him from founding it in his own name, so Kiara, a licensed mental health counselor, obtained an insurance license and set the business up. Kiara Caudill is the company's chief executive officer.[2][5][22] In a 2021 press release he said the company was a response to "a lack of access to annuity educational materials and products" that had "hindered a widespread adoption of annuities in the United States."[15]

The company operates as an independent multi-carrier annuity marketplace offering fixed, multi-year guaranteed, fixed indexed, registered index-linked and variable annuities directly to consumers, with a licensed producer handling the purchase itself.[9][11] The company states that it is licensed in 47 states and represents more than 90 insurance carriers and about 1,500 products, and it reported more than $130 million in premium placed between 2020 and 2025.[5][8][11][24] It has held an A+ rating and accreditation from the Better Business Bureau since February 2022, and its registered address is now in Hamlet, Indiana.[3] Its analysis of 2020 annuity sales is cited in the English Wikipedia article on equity-indexed annuities.[19]

Calculators, guides and Andy Annuity

The company credits Caudill with designing its suite of 17 annuity calculators, covering fixed and multi-year guaranteed annuities, immediate income and deferred income, which he says grew out of client questions: "Every calculator on the site exists because a real client once asked a question I couldn't answer with the tools that were out there."[11] The company also publishes a weekly rate newsletter, a library of more than 300 carrier brochures and a 38-page Deferred Annuity Buyer's Guide updated annually; the 2026 edition was cited by TheStreet in a comparison of multi-year guaranteed annuities with savings accounts.[11][17][25]

In May 2026 the company launched Andy Annuity, a free research assistant built on Anthropic's Claude model and trained on 146 carrier brochures together with live multi-year guaranteed annuity rates.[14] Announcing it, Caudill said that "most retirees still get their first annuity education from a salesperson sitting across a kitchen table," and described the tool as the only case he knew of in which an independent brokerage had "wired live rates, carrier brochures, and a real producer handoff into a single AI-powered conversational interface."[14]

Podcast and Annuity Journal

The My Annuity Store Podcast, listed under Caudill's name on Apple Podcasts and Spotify, began releasing episodes in mid-2025 and is updated several times a week.[21] Most episodes are AI-narrated discussions of the company's own articles and guides; some feature Caudill and the company's vice president, Ryan McGee, on topics such as Federal Reserve rate decisions.[21] In April 2026 Caudill founded Annuity Journal, published at annuityjournal.org, which describes itself as "an independent financial media publication focused on helping Americans make informed decisions about annuities and retirement income"; his author page lists him as founder of both sites.[4][23]

Approach and views [edit]

Caudill's public statements return to one theme: that annuity buyers should be able to research products before they are treated as sales prospects. "Clients shouldn't have to be a lead before they can learn," he told Insurance Business Review. "We prefer they learn everything before they call us, and the more they can learn, the easier it is for us."[9] In a September 2026 release he put the company's founding idea the same way: "We wanted to build a marketplace where people could buy an annuity, not be sold one."[11] He argues that technology should absorb the comparison and explanation work so that "the human conversation can focus on suitability, retirement goals and the decisions that truly require judgment," and that the industry "does not need less human guidance" but "better-informed conversations."[12]

In a 2026 first-person column for Insurance Business Review, written after LIMRA reported record U.S. annuity sales of $461.3 billion for 2025, he attributed the growth to demand for principal protection and argued that an independent platform with published rates removes friction from the buying process.[13] On his personal site he lists search engine optimization alongside annuity distribution and product design among his working competencies.[6]

Reception [edit]

Coverage of Caudill by name comes almost entirely from company press releases and from the two Insurance Business Review award profiles, which the magazine states were developed from interviews with him.[9][10][11] Independent editorial mentions, in ThinkAdvisor, TheStreet and an Insider Monkey ranking republished by Yahoo Finance, cite My Annuity Store as a data source rather than quoting him.[16][17][18] The company's press page also lists Investopedia, Seeking Alpha and MarketWatch among its citations; those items are not documented here.[8]

The company's published production figures match its internal records: a production report reviewed for this article confirms the more than $130 million in premium placed and the more than 400 clients stated on the company's site.[5][8][28] Career totals are separate figures and are self-reported: Caudill's "$1 billion" covers premium he placed personally over his career, and a 2025 release combined the founders' distribution history as $1.5 billion.[4][8][11] Titles differ by source: FINRA records his Raymond James position as registered associate where his biography says regional marketing director.[1][4] Against that, the company's rate tables and sales analyses are the material outside writers have chosen to cite, and his BrokerCheck record is clean across eight years of registration.[1][16][17][19]

Media and recognition [edit]

Personal life [edit]

Caudill is married to Kiara Caudill, CEO of My Annuity Store; a company video describes the business as run by "a husband and wife combo."[22] Kiara Caudill holds a master's degree in psychology from Valparaiso University, practiced for ten years as a licensed mental health therapist, and remains the company's primary fixed annuity producer.[5][15][24] The couple live in Hamlet, Indiana, having previously lived in Fishers, a suburb northeast of Indianapolis.[3]

See also [edit]

Not to be confused with Jason Caudill, professor of business at King University in Tennessee; Jason R. Caudill, an attorney in St. Louis, Missouri; or other people of the same name.

References [edit]

  1. "Jason Todd Caudill, CRD# 5026993". FINRA BrokerCheck detailed report. Retrieved 16 September 2026.
  2. "My Annuity Store, Inc., Indiana Business ID 202001071365796". Indiana Secretary of State business-entity record, mirrored at City-Data. Retrieved 16 September 2026.
  3. "My Annuity Store, Inc. – Business Profile". Better Business Bureau. Retrieved 16 September 2026.
  4. "Jason Caudill, MBA – Founder". My Annuity Store author page. Retrieved 16 September 2026.
  5. "About My Annuity Store". My Annuity Store. Retrieved 16 September 2026.
  6. "Jason Caudill, MBA". Personal website. Retrieved 16 September 2026.
  7. "Jason Caudill, MBA". LinkedIn. Retrieved 16 September 2026.
  8. "Press and Media". My Annuity Store. Retrieved 16 September 2026.
  9. "My Annuity Store | Top Multi-Carrier Annuity Platform 2026". Insurance Business Review. Retrieved 16 September 2026.
  10. "My Annuity Store Named 'Best Multi-Carrier Annuity Platform for 2025' by Insurance Business Review". MarketersMEDIA Newswire via Barchart, 6 November 2025; also carried by InsuranceNewsNet. Retrieved 16 September 2026.
  11. "My Annuity Store Named Top Multi-Carrier Annuity Platform for Second Consecutive Year". ACN Newswire via FinancialContent, 16 September 2026. Retrieved 16 September 2026.
  12. "Annuity Distribution Is Entering Its Transparency Era and My Annuity Store Is Helping Drive the Change". EIN Presswire, 16 September 2026. Retrieved 16 September 2026.
  13. Jason Caudill, "Americans Are Choosing Certainty, and We're Making It Easier to Find". Insurance Business Review, Insights series, 2026. Retrieved 16 September 2026.
  14. "My Annuity Store Launches a Free AI Annuity Research Assistant Trained on 146 Carrier Brochures and Live Annuity Rates". EIN Presswire via The National Law Review, 14 May 2026. Retrieved 16 September 2026.
  15. "How My Annuity Store Inc. is Providing Access to Retirement Planning, Income Solutions, and Annuity". ABNewswire, 5 August 2021. Retrieved 16 September 2026.
  16. Allison Bell, "Will All Annuity Issuers Move to Bermuda?". ThinkAdvisor, 22 December 2021. Retrieved 16 September 2026.
  17. Damilola Esebame, "Retirees may earn more with a MYGA than a savings account". TheStreet, 14 March 2026. Retrieved 16 September 2026.
  18. Fatima Farooq, "10 Best Annuity Companies In the US". Insider Monkey, republished by Yahoo Finance, 19 February 2023. Retrieved 16 September 2026.
  19. "Equity-indexed annuity". Wikipedia, reference to "2020 Annuity Sales Trend Towards Accumulation W/ Protection", My Annuity Store, 12 March 2021. Retrieved 16 September 2026.
  20. "Jason Caudill (Q139783072)". Wikidata. Retrieved 16 September 2026.
  21. "My Annuity Store Podcast". Apple Podcasts; and Spotify. Retrieved 16 September 2026.
  22. "My Annuity Store, Inc." (video description). My Annuity Store on YouTube, 16 July 2025. Retrieved 16 September 2026.
  23. "About". Annuity Journal. Retrieved 16 September 2026.
  24. "Licenses". My Annuity Store. Retrieved 16 September 2026.
  25. "2026 Annuity Buyer's Guide". My Annuity Store. Retrieved 16 September 2026.
  26. "My Annuity Store, Inc.". Wealth & Finance International, Global Insurance and Risk Management Awards 2021 winners list. Retrieved 16 September 2026.
  27. "Insuring Indiana: A Spotlight on the State's Pioneering Insurance Companies". Best Startup US, 28 November 2023. Retrieved 16 September 2026.
  28. "Book of business" production report, My Annuity Store, Inc., generated 16 September 2026. Internal company record provided by the subject and reviewed by the editors in October 2026; not publicly available.

External links [edit]

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