Jon Callaghan

Very early stage venture capitalist

📍 United States🔄 Updated September 2026💼 20 investments📅 23 years investing🗓 Last invested Dec 2023
VC🌍 United States20+ investments
20
Total investments
15
Early stage
1
Mid stage
0
Late stage
23y
Years active

Portfolio

19 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Investor, Board Member
Dec 2023
daydream builds your organic growth engine for the AI Search era. We identify search patterns, create content at scale, and automatically improve that content to drive traffic to your site and grow your presence in AI Search Results (ChatGPT, Gemini, Perplexity, Claude).
Investor, Board Member
Dec 2023
Daydream is a new AI-powered search and discovery platform poised to change the way people shop online. With the largest branded fashion catalog, we are building the most intelligent and personalized shopping experience out there... Its a new era of shopping.
Investor, Board Member
Nov 2022
Ernesta is on a mission to bring gorgeous, designer quality, custom-sized rugs to homes and places of gathering through a delightful, seamless experience. An intentional purchase journey ensures each customer is thrilled with their made-to-measure rug and its truly custom fit. We believe that high-quality design shouldnt be out of reach and we are here to fill this gap in the multi-billion dollar global rug industry.
early stageRetail
Investor, Board Member
Dec 2019
For years, Pipedream has been the go-to integration platform for developers. We built a serverless, source-available, and ridiculously fast workflow engine that tens of thousands of customers use to run millions of mission-critical workflows. Pipedream remains the professional-grade tool for connecting APIs, transforming data, and shipping integrations with code-level control. But we saw the power developers unlocked and asked: “How can we give this to everyone?” The answer wasn’t a simpler version of Pipedream, but a completely new product. Introducing String.com - The AI agent builder. Its a platform where anyone - operators, marketers & founders - can automate complex tasks using plain English. Simply describe what you need done, and String builds and runs the workflow for you. String is powered by the same robust infrastructure that developers trust with Pipedream, but with an interface as simple as typing an email.
Investor, Board Member
Aug 2017
Aisera’s products are delivered as part of Automation Anywhere’s Agentic Process Automation (APA) system, enabling autonomous support for IT, HR, customer service, and more at enterprise scale. creating a unified technology stack purpose-built for the Autonomous Enterprise. Aisera’s products and solutions deliver value at some of the world’s most prominent brands and Fortune 500 enterprises, including Adobe, Aramark, Workday, T-Mobile, Gilead, Amgen, and BNSF Railway. Organizations using Aisera see quantifiable outcomes: up to 63% annual cost savings, 55%+ higher employee productivity, 78% employee satisfaction, and 84% auto-resolution rates across all requests.
Board Member, Investor
2016
Top-performing businesses have one thing in common: better decisions. In fact, decision effectiveness drives 95% of financial performance. Cloverpop is the leading enterprise decision intelligence platform that turns complex decisions into clear outcomes — 2–4X faster and with up to 5X higher shareholder returns. Scale faster, more consistent decisions using AI-powered insights while breaking down silos across your organization. Augment your collaborative decision-making teams with powerful AI decision agents, combining the best of human expertise and AI automation.. Most valuable of all, track decision-making results to learn from past choices and continuously improve your decision-making processes. Recognized in the 2024 Gartner® Decision Intelligence Platforms Market Guide and featured in the 2025 Gartner® Hype Cycle for AI in IT Service Management. Ready to elevate how your organization makes decisions? Schedule a demo today at www.cloverpop.com/contact-us
Board Member
2015
Peloton is at the forefront of connected fitness, with a powerful and thriving community with Members across the US, UK, Canada, Germany, and Australia. Peloton brings together the best equipment, software, content, and instructors to make fitness accessible, effective, and convenient for everyone, while fostering the social connections that keep our Members motivated and moving towards their goals. Through its immersive fitness ecosystem, Peloton is transforming the way people work out with a vast library of live and on-demand studio classes available to take wherever and however our Members choose to move—through Peloton Bike, Bike+, Tread, Row, Guide, and App, and on any iOS and Android device and select smart TVs. Style-forward and body-inclusive, Peloton Apparel is designed to move with you towards all your goals. And with Peloton Corporate Wellness or Peloton Commercial, organizations and enterprises can also access the Peloton platform—bringing the power of interactive fitness to their teams and customers. Innovation-driven and entertainment-led, Peloton is so much more than an exercise brand. It is a global leader at the intersection of fitness, technology, and media.
Venture Capital Investor
May 2013
Screenhero lets you screen share any application with anyone, no matter where they are. Its super simple and blazing fast. You each get your own mouse pointer, and youre both always in control. Its designed for collaboration, not just broadcasting your screen. Its like Google Docs for any application on your computer.
Investor, Board Member
Apr 2013
We’re disrupting a $50 billion industry. Since 2013, we’ve offered our clients the option to truly own their beauty with a revolutionary choice—your place or ours? At home hair color or Hair Color Bar services? Our business is truly omnichannel, with the option to order or subscribe through our website, pick up in store at our Hair Color Bars, or make an appointment at one of our Hair Color Bar locations. At our Hair Color Bars, clients can choose from a variety of color services from licensed cosmetologists—permanent hair color, roots only, hair gloss, highlights and more. With the launch of our men’s line in 2020, we’re shaking up the $50 billion hair care industry with products that continue to raise the bar for doing your own hair at home. We live our values. Here at our San Francisco headquarters and in every Hair Color Bar nationwide, we truly live our values—Love, Joy, Courage, Responsibility, and Trust. Our values inform everything we do, from how we treat our clients to how we treat every member of our fast-growing team. Our founder & CEO, Amy Errett, has fostered a one-of-a-kind culture based on transparency, accountability, and fun; where diversity and inclusion are of utmost importance and every team member feels supported to succeed. We are hair color that breaks the rules. Our commitment to the ultimate client experience, paired with our dedication to product innovation and the latest beauty technology, has attracted a devoted, consistently-growing base of fans, converts, and color evangelists. We love what we do—and it shows. Join us in our mission to live life colorfully and make personal care more personal.
Investor
2011
ToyTalk is an award-winning entertainment and technology company that combines art and science to create conversation with characters. PullString, ToyTalk’s industry-leading technology platform for creating conversation with characters, is putting the power of speech recognition and artificial intelligence into the hands of creative teams at many of the world’s leading entertainment companies. The Winston Show is an iPad app in which kids and characters have real conversations in a new dimension of make-believe. SpeakaZoo is the only zoo where you talk with the animals, and is available for iOS and Android devices. SpeakaLegend is the first-ever talk & touch speech recognition app. Befriend legendary creatures on a quest to find the Unicorn! And SpeakOrTreat lets you visit the scariest neighborhood in town to fill up your candy bag. All apps are available in the App Store.
Angel Investor
2011
At Stio, we create gear that embodies the true essence of mountain life from our hometown of Jackson, Wyoming. Our elevated, responsibly designed styles range from the epic to the everyday and are inspired by an ecosystem that blends natural connection and active balance. We are rooted at the base of the Tetons so we can see mountains, access trailheads and hear spring creeks daily to feed our souls and keep us grounded. This shared mindset of nature, access and balance resonates far beyond our peaks and valley, directly to your mountain life community across distance, geography and topography. For Career and Internship Opportunities, visit stio.com/careers
Investor, Board Member
May 2009
PayNearMe builds technology to transform the payment experience for businesses and their customers. With PayXM™, the industry’s first platform purpose-built for Payment Experience Management, every touchpoint of the payment journey is simple—driving satisfaction, accelerating payments, and lowering the total cost of acceptance. A single platform, contract and integration supports all major payment types and channels, from PayPal, Venmo, Cash App Pay, Apple Pay and Google Pay to cards, ACH and cash at over 62,000 U.S. retail locations. Thousands of non-commerce businesses across industries, including consumer lending, iGaming and online sports betting, property management, and tolling, trust PayNearMe to deliver a complete, seamless payment experience. PayNearMe is offered by PayNearMe MT, Inc., which is a wholly owned subsidiary of PayNearMe, Inc. Follow PayNearMe on X and Facebook. © 2025 PayNearMe Inc. All rights reserved. Money transmission services are provided by PayNearMe MT, Inc, a wholly owned subsidiary of PayNearMe, Inc.
Board Member, Investor
2009
Milo is the leading local shopping search with three million products in 50,000 stores across the U.S. Milo shows you whats locally in-stock now. Become a fan @ http://www.facebook.com/MiloShopping. Milo aggregates the hard-to-find information that millions of consumers are searching for everyday. According to the US Department of Commerce, e-commerce in 2008 accounted for only 3.3% of US retail sales whereas over 87% of US consumers research online and buy offline, according to BIGresearch. Jupiter Research estimates that online product research will impact 40% of total U.S. retail sales by 2011 leading to $1 trillion in sales. Milos team hails from Google, Apple, and other technology leaders, and was backed and advised by some of Silicon Valleys most prominent entrepreneurs, including from Facebook, Paypal, Blekko, and YouTube before its sale in early December. Milo.com is now part of the eBay family, and continues to work towards its mission of bringing every product, of every shelf, of every store onto the web!
Investor, Board Member
Sep 2008
Weve hopped over to @google! Follow us there for all the latest from Fitbit.
Investor, Board Member
Nov 2007
Goodreads is the world’s largest site for readers and book recommendations. Founded in 2007, Goodreads is where readers find and share books they love. Used by avid and casual readers alike, Goodreads members can discover new books by seeing what their friends are reading or by using the Goodreads Book Recommendation Engine; share ratings and recommendations; track what they have read, and list what they want to read. Goodreads is also a place where authors connect with readers. Goodreads is a subsidiary of Amazon. Did we mention we are hiring? We are a team of 110+ people that are passionate about reading and technology, and looking for extraordinary people to join our team. Check out our open positions at www.goodreads.com/jobs
Show all 19 investments ↓
Experience · 22 entries
All (22)
Investments (20)
Founder (1)
Board (16)
2023
Investor, Board Member
Dec 2023
daydream builds your organic growth engine for the AI Search era. We identify search patterns, create content at scale, and automatically improve that content to drive traffic to your site and grow your presence in AI Search Results (ChatGPT, Gemini, Perplexity, Claude).
Investor, Board Member
Dec 2023
Daydream is a new AI-powered search and discovery platform poised to change the way people shop online. With the largest branded fashion catalog, we are building the most intelligent and personalized shopping experience out there... Its a new era of shopping.
2022
Investor, Board Member
Nov 2022
Ernesta is on a mission to bring gorgeous, designer quality, custom-sized rugs to homes and places of gathering through a delightful, seamless experience. An intentional purchase journey ensures each customer is thrilled with their made-to-measure rug and its truly custom fit. We believe that high-quality design shouldnt be out of reach and we are here to fill this gap in the multi-billion dollar global rug industry.
early stageRetail
2019
Investor, Board Member
Dec 2019
For years, Pipedream has been the go-to integration platform for developers. We built a serverless, source-available, and ridiculously fast workflow engine that tens of thousands of customers use to run millions of mission-critical workflows. Pipedream remains the professional-grade tool for connecting APIs, transforming data, and shipping integrations with code-level control. But we saw the power developers unlocked and asked: “How can we give this to everyone?” The answer wasn’t a simpler version of Pipedream, but a completely new product. Introducing String.com - The AI agent builder. Its a platform where anyone - operators, marketers & founders - can automate complex tasks using plain English. Simply describe what you need done, and String builds and runs the workflow for you. String is powered by the same robust infrastructure that developers trust with Pipedream, but with an interface as simple as typing an email.
2018
Venture Capital Investor
Nov 2018
sweetgreen is a destination for real food. We believe the choices we make every day about what we eat, where it comes from, and how it’s made have a lasting impact on our communities. From the seed to the store, we’re involved in every step of the supply chain, working with partners and farmers we know and trust. We make our food from scratch in each sweetgreen every day, using whole produce delivered that morning. As sweetgreen grows, we’re dedicated to working with the right people. We’ve built a team of over 5,000 hardworking individuals who care about developing future leaders and live our core values daily. We meet farmers before we meet landlords. We turn our new neighbors into friends. We’re building a brand that connects to local neighborhoods and leaves communities better off than we found them. Our mission is to inspire healthier communities, by connecting people to real food. With over 220 locations across PA, MA, DMV, NY, CA, IL, TX, CO, and FL, we’ve worked hard to build a company with passion and purpose - and we’re just getting started.
Show all 22 entries ↓
Investment activity
2003–2023 · 20 investments
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