Participated · Equity · Jul 2022

Inflection Points is a crypto-focused employment and corporate training business that connects crypto companies with talent and provides corporate training. The firm was founded by Colton Sakamoto and Anthony Pompliano and operated in stealth for 18 months before emerging publicly. It acquired crypto-focused recruiting agency Proof of Talent and says it has helped over 1,000 people secure jobs at firms including Coinbase, Gemini and Kraken. The company has been profitable since inception and raised outside funding after it hit seven figures in revenue. Long term, the founders expect substantial job growth in the crypto space as large tech firms and service providers build blockchain products and expand offerings. The founders' public profiles and Pompliano's network are cited as strategic assets for sourcing candidates and investor support.

Led · Series D · May 2022

Booster Fuels operates a mobile gas service that delivers fuel directly to fleet and consumer vehicles in parking lots, serving more than 500 fleets including Amazon, UPS and Imperfect Foods. Founded in 2015, the company began by partnering with employers to fuel employee vehicles in private corporate lots and later expanded into fueling large logistics carriers and their contractors. Booster offers renewable diesel and last year rolled out on-demand electric vehicle charging; the company says customers typically see 4–8% reductions in fuel consumption by eliminating unnecessary trips and fuel theft. Its revenue grew 125% year‑over‑year in Q1, and the company employs more than 400 people. Booster maintains a consumer business in addition to its fleet operations, and CEO Frank Mycroft said rising fuel prices and energy concerns have helped accelerate customer conversion to renewables. Booster operates an on-demand mobile fueling service using high-tech purple mini fuel tankers and service professionals to deliver gas and diesel directly to personal cars and fleets. The company runs a proprietary FuelOS platform with sophisticated routing and has become a 24/7 fleet and consumer service in more than 20 cities, serving tens of thousands of customers and completing over 2 million deliveries. Booster has expanded into fleet fueling with customers including Stanley Steemer, Two Men and a Truck, Hardin Honda, and Traffic Management Inc., and is used by Fortune 100 employers in its markets. The company highlights environmental benefits — it says it has prevented over 2.32 million pounds of carbon release and a May 2019 ALG study found a 26% reduction in VOC emissions versus retail gas stations. Booster plans to expand into the Pacific Northwest and the East Coast to unlock new markets and modernize fueling infrastructure. The company has raised capital to support that growth, with total funding now at $88.5 million. Booster operates an app-based mobile fueling service that schedules gas truck visits to office parking lots, commuter campuses and other private communities so employees can have their cars filled while at work. Customers sign up in the app, schedule a fill-up, leave the gas cap open, and pay Booster directly; the company says it often charges about ten cents per gallon less than station prices. Booster has secured partnerships with employers including Cisco, Oracle and Facebook and is focused on private communities rather than servicing the general public. The company positions the service as more convenient, safer and more sustainable than traditional refueling, and aims to modernize the gasoline habit for the 21st century. Financially, Booster has raised a $20 million Series B and $32 million in total funding to date. Company leadership and investors cite distribution efficiency, regulatory expertise and technology innovation as competitive advantages. Booster Fuels partners with large employers to offer on-demand fuel service on corporate campuses through a mobile app; employees request a fillup, leave the gas cap open, and return to a filled tank. The company operates drivers who are commercial, background-checked, and handle Regular and Premium Unleaded fuel. Booster purchases fuel wholesale and says its prices are competitive with, and often lower than, local gas stations. Booster has expanded beyond its home state of Texas into California, where it began working with Chegg. At Chegg, 65 percent of employees regularly use Booster and the service filled 100 cars on its busiest day. The company aims to eliminate the need to visit gas stations for a large share of drivers and improve employee quality of life on car-dependent campuses. Booster Fuels is a Seattle-based startup operating in the transportation industry and led by CEO and co-founder Frank Mycroft, formerly VP of Strategy at Planetary Resources. The company is secretive about its product, saying only that it has a “very massive vision that will positively impact the globe.” GeekWire uncovered the firm's $3.1M funding through an SEC filing, and Mycroft confirmed the investment. Investors include Madrona Venture Group, Planetary Resources co-founder Eric Anderson, and other angel backers. Corporate records list Anderson as chairman and Madrona’s Matt McIlwain as a director. The startup has a “handful of employees” and a bare-bones website with only a logo and a sign-up form.

Led · Series A · May 2022

Cushion provides an app that helps U.S. consumers negotiate bank and credit card fees and is expanding into bill pay to offer a single place to track, pay, and finance bills. The company reports more than 100,000 current customers and an additional six-figure waitlist for the new bill pay product. After months of beta testing, Cushion is preparing the bill pay solution for a general audience. Proceeds from its financing will be used to hire across product, engineering, data analytics, and marketing to support the rollout. Led by CEO Paul Kesserwani and based in San Francisco, Cushion aims to help consumers avoid overdraft and late fees through its bill management and fee-negotiation services. Cushion offers a consumer app that downloads users' transaction histories, identifies assessed bank fees, and conducts negotiations with banks to secure refunds. The company only takes a commission on returned cash, aligning its incentives with customers. Founder Paul Kesserwani formed Cushion in late 2016 and built its own infrastructure to avoid using Plaid, launching a new platform in early January 2018. Cushion says it has onboarded tens of thousands of users and has recovered more than $1 million in fees for customers since founding. The company raised seed capital and is hiring engineers and data scientists to build out AI recommendations. Longer-term plans include broader active management features—switching users to lower-fee accounts, adjusting bill timing to avoid shortfalls—and potentially working directly with banks to offer lower-cost customer service channels.

Led · Series B · Jan 2022

Merit, originally founded as Sigma, has built a software platform that connects directly to government licensing databases and converts paper or plastic credentials—such as driver’s or professional licenses—into secure, digital records that can be instantly verified by third parties. Over the past five years the company has developed custom connectors for multiple state and local agencies, enabling automatic updates so credentials stay current without manual checks. A prominent showcase was its rapid deployment after the Miami building collapse, where Merit verified access permissions for more than 16,000 responders and vendors in a single month. The fully remote startup currently employs around 70 people and expects headcount to reach roughly 100 by year-end, using its distributed model to improve diversity in hiring. While specific revenue figures are not disclosed, Merit’s business model centers on selling its verification services to government entities and the private organizations that rely on those credentials. The fresh capital will help expand integrations with additional government agencies and accelerate product enhancements for broader adoption.

Led · Series A · Dec 2021

Tava Health operates a technology-driven behavioral health platform that connects clinicians, employers, and health plans and offers tools across the care lifecycle. The company recently launched Symphony by Tava Health, an AI-assisted practice management system for clinicians; TavaCare for Employers, which can be fully sponsored or used with existing insurance without per-employee fees; and Tava Guide, a referral and care-tracking hub for payers and systems. Tava reports integrations with more than 200 health plans and claims in-network reach for nine in 10 commercially insured Americans, with first-session availability in as little as 12 hours. It also reports that 87% of its clients show measurable clinical improvement. The company says its platform is designed to reduce administrative burden for clinicians while removing cost barriers for employers. The new Series C funding will support deeper investment in partners and continued platform expansion.