Tom Montgomery 🤜🤛

Founder at Chubbies + Loop Returns | Sharing lessons from building 9-figure businesses and 10-figure outcomes

📍 United States🔄 Updated September 2026💼 11 investments📅 14 years investing🗓 Last invested Sep 2024
VC🌍 United States
11
Total investments
6
Early stage
1
Mid stage
1
Late stage
14y
Years active

Portfolio

11 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Board Member
Sep 2024
Small™ is 2.5% ABV beer for people with sh*t to do. PS were hiring... Visit https://beerstreetbrands.com for details.
early stageBreweries
Investor
2021
Fairing (formerly EnquireLabs) brings speed & scale to zero-party data so Ecommerce brands can build sustainable customer relationships and growth models. Marketing attribution, segmentation & personalization, CRO and more — delivered through the ground truth of survey data and operationalized for automation & integration. Trusted by thousands of Ecommerce brands.
Investor
2021
Rupert helps data analysts quickly and accurately surface the scenarios that matter most to their stakeholders with our no-code alert builder. With Rupert, accelerate any time sensitive data-driven workflow with precise, real-time alerts. For example: Identify and respond to operational issues or SLA breaches faster to keep internal processes on track and customer satisfaction high Unblock sales or onboarding funnels more effectively by reacting right away when a valuable prospect or user is not progressing to the next stage Monitor customer accounts for any activity, health, churn, or upsell signals you chose, so your account managers easily can provide highly-responsive, white glove service that keeps and grows your accounts --- Analysts deserve the flexibility and control to deliver timely, personalized, data-rich alerts. No ETL. No engineering. No noise. Try Rupert today
Investor
2021
​​Constructor is the only search and product discovery platform designed exclusively for commerce where conversions matter. Our platform delivers unmatched KPI optimization and fast ROI for enterprise ecommerce brands, retailers, distributors, marketplaces, and more — while giving customers a personalized, enjoyable shopping experience. Unlike other platforms, Constructor is the only search and product discovery solution that was built from the ground up with clickstream data and advanced AI, not merely bolted onto a legacy keyword engine. Consistently outperforming competitors by an average of 3% in A/B tests, Constructor’s cloud-based solutions harness the power of natural language processing, machine learning, collaborative personalization, and Generative AI to deliver compelling user experiences across all aspects of product discovery. From search to browsing, recommendations, collections, merchant intelligence, quizzes, attribute enrichment, and AI shopping assistants, Constructor covers the entire discovery journey. Optimizing specifically for ecommerce metrics like revenue, conversion rate and profit, Constructor generates consistent $10M+ revenue lifts for our customers, which include some of the world’s most recognized brands, like Sephora, Petco, Bonobos, Target Australia, Birkenstock, The Very Group, and many more. Constructor was named a Strong Performer in The Forrester Wave™ for Commerce Search And Product Discovery, Q3 2023, and a Visionary in the First-Ever Gartner Magic Quadrant for Search and Product Discovery. Constructor also recently received multiple G2 Summer 2025 badges—including Grid Leader for E-Merchandising, E-Commerce Personalization, High Performer for Enterprise, and Best Support.’ Learn more at constructor.com.
Investor
2021
Status powers the customer accounts experience for Shopify Plus brands like Princess Polly & LSKD. Brands using Status... - Eliminate passwords & keep accounts logged-in up to 6 months. - Integrate their tech stack inside one login experience. - Drive more customers to shop while logged-in. - Increase AOV, LTV, and CVR. See how Status has generated 2,000,000+ signed-in shoppers 👇
Investor
2020
💻 A Unified Platform for Global eCommerce Operations 💻 It’s been our mission to create the best end to end supply chain platform for direct to consumer businesses. ✪ Specialties ✪ ● Direct To Consumer Brands ● ERP ● Inventory Management ● Order Management ● 3PL, WMS ● Product Information Management ● Marketplace Contact: ✉ Email: letsgo@channelape.com
Investor
2020
Were on a mission to help retailers navigate the complex, competitive and ever-changing retail landscape. Toolio is a cloud-based Merchandising Platform that automates critical workflows, provides real-time insights, and enables remote collaboration, empowering retailers to make faster, data-driven decisions about their most important (and expensive) asset—inventory. Toolio is a global operation with headquarters in NYC and offices in Istanbul, built by an ex-Walmart team of second-time entrepreneurs and backed by top VCs and apparel industry executives. Hop on the rocket ship and learn how Toolio can help your team navigate the future by visiting toolio.com.
Investor
2020
Unify your online retail strategy with Carro’s Dropship Platform, built for retailers looking to expand their product catalog without the burden of inventory. Carro enables retailers to bring their own partners onto one platform to connect, collaborate, and grow profitably by unlocking new sales channels. With Carro, Retailers can sell more products across their own storefronts without inventory risk, and Brands can distribute products through trusted retailer partners. In the end both sides can expand reach into new audiences, platforms, and regions.
Investor/Advisor
2019
Viralspace uses AI to help digital marketers make data-driven decisions about their ad creative. Our mission is to take the guesswork out of the advertising process and empower creatives with data. Founded in 2018, our investors and supporters include Lightspeed Venture Partners and Village Global (a fund backed by Bezos, Gates, and Zuckerberg), Quest Venture Partners, Plug and Play, and Switch VC.
Investor
2018
JuneShine
early stageFood & Beverages
Investor
Jan 2012
Tortuga AgTechs mission is to build a healthier society, and a thriving ecosystem, through smarter farming. We provide harvesting and other services to fruit & vegetable farmers through our robotics and software. We are venture-backed by leading investors in Silicon Valley, and proud to be based in Denver, CO.
early stageFarming
Experience · 16 entries
All (16)
Investments (11)
Founder (3)
Board (1)
2024
Board Member
Sep 2024
Small™ is 2.5% ABV beer for people with sh*t to do. PS were hiring... Visit https://beerstreetbrands.com for details.
early stageBreweries
2023
Founder
Sep 2023
Build your moat. As a consumer business, Brand is your only long-term moat and everything you do builds (or erodes) that moat. Protect your economic castle with the only constantly-learning ML measurement platform that quantifies the long-term incremental baseline revenue impact of your moat-building.
2021
Investor
2021
Fairing (formerly EnquireLabs) brings speed & scale to zero-party data so Ecommerce brands can build sustainable customer relationships and growth models. Marketing attribution, segmentation & personalization, CRO and more — delivered through the ground truth of survey data and operationalized for automation & integration. Trusted by thousands of Ecommerce brands.
Investor
2021
Rupert helps data analysts quickly and accurately surface the scenarios that matter most to their stakeholders with our no-code alert builder. With Rupert, accelerate any time sensitive data-driven workflow with precise, real-time alerts. For example: Identify and respond to operational issues or SLA breaches faster to keep internal processes on track and customer satisfaction high Unblock sales or onboarding funnels more effectively by reacting right away when a valuable prospect or user is not progressing to the next stage Monitor customer accounts for any activity, health, churn, or upsell signals you chose, so your account managers easily can provide highly-responsive, white glove service that keeps and grows your accounts --- Analysts deserve the flexibility and control to deliver timely, personalized, data-rich alerts. No ETL. No engineering. No noise. Try Rupert today
Investor
2021
​​Constructor is the only search and product discovery platform designed exclusively for commerce where conversions matter. Our platform delivers unmatched KPI optimization and fast ROI for enterprise ecommerce brands, retailers, distributors, marketplaces, and more — while giving customers a personalized, enjoyable shopping experience. Unlike other platforms, Constructor is the only search and product discovery solution that was built from the ground up with clickstream data and advanced AI, not merely bolted onto a legacy keyword engine. Consistently outperforming competitors by an average of 3% in A/B tests, Constructor’s cloud-based solutions harness the power of natural language processing, machine learning, collaborative personalization, and Generative AI to deliver compelling user experiences across all aspects of product discovery. From search to browsing, recommendations, collections, merchant intelligence, quizzes, attribute enrichment, and AI shopping assistants, Constructor covers the entire discovery journey. Optimizing specifically for ecommerce metrics like revenue, conversion rate and profit, Constructor generates consistent $10M+ revenue lifts for our customers, which include some of the world’s most recognized brands, like Sephora, Petco, Bonobos, Target Australia, Birkenstock, The Very Group, and many more. Constructor was named a Strong Performer in The Forrester Wave™ for Commerce Search And Product Discovery, Q3 2023, and a Visionary in the First-Ever Gartner Magic Quadrant for Search and Product Discovery. Constructor also recently received multiple G2 Summer 2025 badges—including Grid Leader for E-Merchandising, E-Commerce Personalization, High Performer for Enterprise, and Best Support.’ Learn more at constructor.com.
Show all 16 entries ↓
Investment activity
2012–2024 · 11 investments
201212018120191202032021420241
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