Resume

Zero-to-one operator across technology, finance, and startups. Over $20M raised, more than $300M originated, and a full market cycle behind me.

New York, NYrob@rkmasiello.netLinkedInGitHub

Experience

Founder

Dealport
2026 – Present
New York, NY
  • -Building an AI-native platform to make SMB M&A faster and investable.
  • -Building agentic AI systems that automate deal sourcing, diligence, and workflow.
  • -Hands-on across product, engineering, and go-to-market.
AIM&APlatform

Founder

KBOR Systems
2020 – Present
New York, NY
  • -Fractional CTO/CSO practice pairing hands-on technology with business strategy.
  • -Advise founders and teams on architecture, AI strategy, positioning, and fundraising readiness.
Fractional CTO/CSOAI StrategyAdvisory

Co-founder & COO → CEO

Arcade.xyz
2021 – 2025
New York, NY
  • -Co-founded and built the first NFT-collateralized lending platform. Grew it to $300M+ in originated loans.
  • -Raised $15M+ from Pantera Capital, Franklin Templeton, and Castle Island Ventures.
  • -Came in as COO and became CEO during a leadership change. Ran the company through a full market cycle.
  • -Built and led a team of 20 across engineering, product, and operations. Owned the budget and P&L.
  • -Handled the parts with no roadmap: entity structuring, share classes, advisor agreements, cross-border operations, and hard legal calls under an unsettled regulatory regime.
FintechMarkets0→1

Director → Strategic Advisor

Industry Capital
2019 – 2025
New York, NY
  • -Joined the ~$3.5B private equity manager after it acquired Riverblock.
  • -Advised on digital infrastructure and crypto-asset strategy, diligence, and portfolio work.
Private EquityInvestingStrategy

Founder

Riverblock
2018 – 2021
New York, NY
  • -Founded an analytics company in the Bitcoin-mining sector and grew it from a side project into a company.
  • -Acquired by private equity firm Industry Capital in 2019. My first exit.
AnalyticsBitcoinExit

Consultant, Big-Data Transformation

BASF · Accenture · Booz Allen · EY
2013 – 2018
Washington, DC / New York, NY
  • -Delivered enterprise big-data and cloud transformation programs for Fortune 500 and federal clients.
  • -Worked with federal agencies including the FDA and U.S. Treasury, and insurance carriers at EY.
  • -Built the systems thinking and institutional fluency behind everything since.
EnterpriseFederalData & Cloud

Education

Bachelor of Science

New Jersey Institute of Technology
2009 – 2013
Newark, NJ

Skills

Building

TypeScriptSwift / Native iOSPythonAI & Agentic SystemsData Systems & Cloud

Operating

Fundraising & Investor RelationsTeam Building & Scaling (1 → 20+)Go-to-MarketBudgets & P&L

Navigating Ambiguity

Legal & Entity StructuringShare Classes & Advisor AgreementsCross-Border OperationsRegulatory Grey Zones

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