Selling online got easy. The part after the sale - knowing what to buy, when, and how much - is still run on 1950s math and Friday-night spreadsheets. Flieber is betting AI can finally do the boring part.
Toolio is a New York-based retail technology company that builds cloud-based, AI-powered merchandising software. Its platform replaces spreadsheet-driven planning with connected workflows for merchandise financial planning, open-to-buy, assortment planning, demand forecasting, and allocation. Founded in 2019 by ex-Walmart engineers Eytan Daniyalzade and Berk Atikoglu, Toolio helps modern retailers and direct-to-consumer brands decide what to buy, how much, and where to place it - managing over a billion dollars of inventory across more than 100 retail customers.
Tyba is a San Francisco-based climate software company that helps energy companies develop, model, and operate battery energy storage projects more profitably. Its AI-driven platform pairs a Project Simulation product - which backtests and forecasts revenue for storage assets in development - with an Asset Operations product that automates real-time bidding and dispatch in wholesale power markets like ERCOT and CAISO. Founded in 2022 by former energy developers and infrastructure engineers, Tyba positions itself as the 'autopilot for batteries,' emphasizing transparent, non-black-box optimization. The company raised a $13.9M Series A led by Energize Capital in February 2025.
Andrej Strojin is the co-founder and CEO of HAVERHILL, a Warren, Rhode Island fine-jewelry house that makes 14k gold, birthstone-personalized pieces to order rather than in advance. A Slovenian-trained mechanical engineer and former Deloitte and Strategy& consultant, he met fifth-generation jeweler Haverhill Leach on a dating app in 2018, married her four months later, and turned her artisan brand into a fast-scaling direct-to-consumer operation. When COVID shut down suppliers before Mother's Day 2020, the couple built a jewelry assembly line in their garage and cut turnaround from seven days to one. Under Strojin the company has quadrupled sales, reached $16M in 2024 revenue, and landed on the Inc. 5000 three years running.
SYSO Technologies is a Boston-based market operations partner for renewable energy and battery storage assets. The company acts as the market operator for solar, wind, and energy storage projects, handling registration, forecasting, bidding, scheduling, real-time dispatch, and settlement across every major North American ISO/RTO market. Its cloud-based, AI-enabled Energy Management Platform turns passive renewable generators into active market participants, and by 2026 SYSO managed more than 4.5 GW across 300+ sites.
Nicholas Speyer is the co-founder and CEO of SYSO Technologies, a Boston-based market operations firm that runs renewable and battery storage assets in the wholesale power markets. Under his leadership, SYSO has grown to manage more than 4.5 gigawatts across 300+ sites in every major ISO/RTO market and into Canada, backed by a $15.5M Series B from Kimmeridge, New Energy Capital and MassMutual Ventures. A Stanford-trained energy resources engineer, Speyer spent two decades building energy-software and efficiency businesses before turning SYSO into what its investors call the clear leader in its space.
Michael Ulin is a three-time AI founder and engineer who builds machine-learning companies in heavily regulated industries. He was the founding AI engineer and VP of AI at ZestyAI, whose property-risk models help underwrite trillions in U.S. insured assets, then co-founded and served as CTO of Paxton AI, a generative-AI legal research tool used by thousands of attorneys that raised a $6M seed round in 2023. He now builds from Bend, Oregon, where his current work centers on Trarian, applying AI to patent underwriting, alongside ventures spanning AI forecasting and probabilistic reasoning. He also writes the Substack 'And Yet It Moves' on entrepreneurship and the case for building startups outside Silicon Valley.