Hilton Advisory Group

Strategic Advisory for Capital,
Growth, and Transformation

Our Team

J. Bradley Hilton

Founder & Managing Director

Michael Woloshin

Founder & Partner

Shane Hackett

Founder & Partner

About Us

Hilton Advisory Group Founded by J. Bradley Hilton, Michael Woloshin and Shane Hackett is an independent advisory firm providing strategic guidance to founders, executives, family offices, and institutions navigating complex business and capital decisions.

We work alongside leadership teams during critical moments—growth initiatives, capital strategy, market entry, restructuring, and strategic transitions—offering experienced perspective, disciplined analysis, and access to a global network of relationships.

Advisory Services​

Strategic Business Advisory
  • Guidance on growth strategy, competitive positioning, and long-term planning for founders and executive teams.
Capital Strategy Advisory
  • Advisory support around capital planning, financing options, balance sheet strategy, and readiness for external capital.
Mergers & Strategic Transactions Advisory
  • High-level advisory on acquisitions, divestitures, joint ventures, and strategic alternatives
    (non-executional).
Market Entry & Expansion Advisory
  • Strategic guidance for entering new markets, launching new products, or expanding into adjacent verticals.
Corporate Structuring & Governance Advisory
  • Advice on organizational structure, governance frameworks, and executive alignment
Technology & Digital Strategy Advisory
  • Advisory services focused on AI, automation, digital platforms, and technology-driven growth initiatives.
Investor & Stakeholder Positioning
  • Strategic guidance on messaging, positioning, and preparation for investor, partner, or board-level discussions.
Introductions to Strategic Partners
  • Discretionary introductions to capital providers, strategic partners, and service professionals where appropriate.

Learn How We Can Help Your Business Today

J. Bradley Hilton

Founder & Managing Director

Bradley Hilton is a founder, strategic advisor, and capital-markets executive with decades of experience working at the intersection of entrepreneurship, finance, and multi-generational business stewardship. As a member of the Hilton family legacy, Mr. Hilton brings a rare combination of institutional perspective, operational discipline, and long-term value orientation to every engagement.

Throughout his career, Mr. Hilton has advised founders, family offices, executives, and growth-stage companies on strategy, governance, capital structuring, and organizational scale. His work spans multiple industries, including technology, real estate, hospitality, media, and emerging growth sectors, with a consistent focus on building durable businesses rather than short-term outcomes.

Mr. Hilton is known for his ability to operate both as a high-level strategist and a hands-on operator. He has worked closely with leadership teams during critical inflection points—early formation, restructuring, expansion, and transition—helping organizations clarify vision, align stakeholders, and execute with precision. His advisory approach emphasizes disciplined decision-making, accountability, and the preservation of enterprise value over time.

Drawing on experience across both private and public markets, Mr. Hilton has played a key role in guiding companies through complex strategic decisions involving partnerships, governance frameworks, capital introductions, and long-range planning. He is particularly respected for his discretion, judgment, and ability to navigate sensitive situations involving founders, boards, and multi-party interests.

In addition to his advisory work, Mr. Hilton has been involved in launching and scaling businesses, serving as a trusted counsel to leadership teams seeking principled guidance rather than transactional advice. His reputation has been built largely through relationships and results, not publicity, and many of his engagements come through long-standing referrals.

Mr. Hilton’s philosophy is rooted in stewardship: building companies that endure, creating alignment between leadership and capital, and ensuring that growth is achieved responsibly and intelligently. He believes that the strongest businesses are those grounded in clear values, sound governance, and thoughtful execution.

As Founder and Managing Director of J. Bradley Hilton Advisors, Mr. Hilton leads the firm’s strategic vision and client engagements, offering senior-level advisory services to entrepreneurs, executives, and organizations seeking clarity, structure, and long-term success. The firm reflects his belief that experience, judgment, and trust are the most valuable assets an advisor can offer.

Michael Woloshin

Founder & Partner

Michael Woloshin is the Founder & Chairman of Digital Innovations Group (DIG), a technology holding company focused on building and scaling advanced AI-driven platforms for marketing, automation, and enterprise growth.

Through DIG, Michael led the development of the IRMA Engine (Internet Reasoning Model Aggregator), an AI-powered platform designed to automate large-scale content distribution, market intelligence, and digital engagement across global channels. The IRMA Engine integrates artificial intelligence, automation, and data-driven workflows to support companies seeking scalable, technology-enabled growth strategies.

In addition to DIG, Michael is the Founder of Recruiter.com and the Founder of NexGenAI Holding Group, organizations focused on building digital infrastructure, automation tools, and next-generation platforms across recruiting, marketing, and enterprise services.

Michael also oversees and manages some of the largest professional communities on LinkedIn, reaching millions of followers across multiple groups, including one of the largest AI-focused groups on the platform with over one million members. These communities connect founders, executives, technologists, and investors globally, providing insight into emerging trends, market sentiment, and real-time industry dialogue.

Throughout his career, Michael has worked closely with founders, executive teams, and strategic partners to design growth strategies, implement technology platforms, and navigate periods of scale, transformation, and operational complexity. His experience spans early-stage platform development through mature enterprise execution, with a focus on long-term positioning rather than short-term outcomes.

Michael’s advisory approach emphasizes structure, clarity, and execution readiness. He works with leadership teams to pressure-test assumptions, align strategy with operational realities, and ensure organizations are properly positioned before engaging capital, partnerships, or expansion initiatives.

At J. Bradley Hilton Advisors, Michael contributes expertise in technology strategy, AI systems, automation, and go-to-market execution, helping clients evaluate opportunities and structure growth initiatives with discipline and foresight.

Shane Hackett

Founder & Managing Partner
Market Leverage

Shane Hackett is a growth strategist, market-structure advisor, and founder of Market Leverage, where he works with companies to design, position, and scale strategies that convert market opportunity into durable traction. With a background rooted in execution, Shane is known for translating complex market dynamics into actionable systems that drive visibility, demand, and sustained growth.

Throughout his career, Shane has worked closely with founders, executives, and leadership teams navigating competitive markets, shifting narratives, and inflection points in scale. His work focuses on understanding how markets actually behave—how attention moves, how capital reacts, how narratives form, and how timing and positioning often matter as much as product or capital itself.

Shane’s approach blends strategic insight with practical execution. He has advised companies on go-to-market strategy, brand positioning, demand generation, audience growth, and leverage-driven expansion, helping organizations avoid common growth traps such as premature scaling, misaligned messaging, and inefficient capital deployment. Rather than chasing visibility for its own sake, his work centers on creating repeatable systems that compound over time.

At Market Leverage, Shane leads engagements that focus on identifying where real leverage exists within a business—whether through market positioning, distribution channels, strategic partnerships, or narrative alignment—and then building frameworks to exploit that leverage intelligently. He is particularly effective at helping companies sharpen their message, clarify their value proposition, and align execution with how their target market actually makes decisions.

Shane is respected for his clarity, directness, and ability to cut through noise. He does not approach advisory work from a theoretical distance, but from an operator’s mindset—testing assumptions, measuring outcomes, and refining strategy based on real-world feedback. His clients value his ability to challenge thinking constructively while remaining deeply invested in execution and results.

As Founder and Managing Partner of Market Leverage, Shane oversees strategy, client engagement, and execution frameworks, working hands-on with leadership teams to ensure that growth initiatives are not only ambitious, but sustainable and defensible.