Capital & commercial advisory for the middle market

Capital & commercial advisory
for the middle market

Advising companies on debt and M&A while building systematic channels for commercial
origination and market access.

Advising companies on debt and M&A
while building systematic channels for commercial origination and market
access.

Advising companies on debt and M&A while building systematic
channels for commercial origination and market access.

Proudly Trusted By

OUR PRACTICES

TWO ADVISORY Arms. ONE ORIGINATION DISCIPLINE.

Breakout operates across two distinct but complementary mandates: advising companies on debt and M&A transactions, and building the commercial origination infrastructure required to access sophisticated buyers and generate qualified opportunities.

01 / CAPITAL ADVISORY

Debt and M&A advisory for middle-market companies.

We advise management teams through debt financings and M&A transactions, from positioning and counterparty identification through diligence, negotiation, and execution.

DEBT ADVISORY · M&A ADVISORY · TRANSACTION EXECUTION

02 / COMMERCIAL ADVISORY

Systematic origination for companies operating in complex markets.

We build the market intelligence, positioning, and distribution infrastructure required to identify qualified counterparties and create a repeatable commercial pipeline.

MARKET INTELLIGENCE · COMMERCIAL POSITIONING · ORIGINATION & PIPELINE

Upward architectural view of Toronto financial-district office towers
Upward architectural view of Toronto financial-district office towers
Upward architectural view of Toronto financial-district office towers

CAPABILITIES

SPECIALIST CAPABILITIES ACROSS CAPITAL AND COMMERCIAL MANDATES.

SPECIALIST CAPABILITIES ACROSS CAPITAL AND COMMERCIAL MANDATES.

SPECIALIST CAPABILITIES ACROSS CAPITAL AND COMMERCIAL MANDATES.

Breakout supports management teams through the intelligence, origination, preparation, and execution required to move complex opportunities forward.

Breakout supports management teams through the intelligence, origination, preparation, and execution required to move complex opportunities forward.

Breakout supports management teams through the intelligence, origination, preparation, and execution required to move complex opportunities forward.

01

CAPITAL

DEBT ADVISORY

DEBT ADVISORY

Structuring and sourcing senior, unitranche, mezzanine, and asset-backed financing from institutional lenders and private credit funds.

Structuring and sourcing senior, unitranche, mezzanine, and asset-backed financing from institutional lenders and private credit funds.

Structuring and sourcing senior, unitranche, mezzanine, and asset-backed financing from institutional lenders and private credit funds.

02

CAPITAL

M&A ADVISORY

M&A ADVISORY

Buy-side and sell-side representation from strategic positioning and counterparty identification through diligence, negotiation, and closing.

Buy-side and sell-side representation from strategic positioning and counterparty identification through diligence, negotiation, and closing.

Buy-side and sell-side representation from strategic positioning and counterparty identification through diligence, negotiation, and closing.

03

CAPITAL

TRANSACTION EXECUTION

TRANSACTION EXECUTION

Preparing companies for market, structuring materials and diligence, and managing counterparties through execution.

Preparing companies for market, structuring materials and diligence, and managing counterparties through execution.

Preparing companies for market, structuring materials and diligence, and managing counterparties through execution.

04

COMMERCIAL

MARKET INTELLIGENCE

MARKET INTELLIGENCE

Defining qualified opportunity criteria and mapping sophisticated buyers, strategic counterparties, and markets with demonstrated fit.

Defining qualified opportunity criteria and mapping sophisticated buyers, strategic counterparties, and markets with demonstrated fit.

Defining qualified opportunity criteria and mapping sophisticated buyers, strategic counterparties, and markets with demonstrated fit.

05

COMMERCIAL

POSITIONING & DISTRIBUTION

POSITIONING & DISTRIBUTION

Establishing the positioning, channel architecture, and institutional guardrails required to access complex markets.

Establishing the positioning, channel architecture, and institutional guardrails required to access complex markets.

Establishing the positioning, channel architecture, and institutional guardrails required to access complex markets.

06

COMMERCIAL

ORIGINATION & PIPELINE

ORIGINATION & PIPELINE

Executing systematic outreach, qualifying counterparties, facilitating introductions, and managing opportunity flow.

Executing systematic outreach, qualifying counterparties, facilitating introductions, and managing opportunity flow.

Executing systematic outreach, qualifying counterparties, facilitating introductions, and managing opportunity flow.

MANDATE FIT

BUILT FOR COMPANIES AT AN INFLECTION POINT.

Breakout advises established and scaling middle-market companies pursuing a material capital event, entering a complex market, or building a more disciplined origination function.

MANDATE PROFILE

PRELIMINARY FIT

STATUS:

STRONG POTENTIAL FIT

OPERATING PROFILE:

ESTABLISHED / SCALING

STRATEGIC CATALYST:

CAPITAL EVENT / COMMERCIAL EXPANSION

MARKET STRUCTURE:

COMPLEX / RELATIONSHIP-DRIVEN

COUNTERPARTIES:

INSTITUTIONAL / SOPHISTICATED

ENGAGEMENT:

SENIOR-LED / CONTROLLED

COMPANY

An established operating business with differentiated capabilities, credible leadership, and demonstrated market relevance.

SITUATION

A debt financing, acquisition, sale process, market entry, or commercial origination mandate with material strategic importance.

MARKET

A complex B2B or institutional environment where qualified access and precise positioning matter more than broad-volume outreach.

ENGAGEMENT

A management team seeking senior advisory involvement, a controlled process, and measurable forward movement.

CAPITAL EVENTS · COMMERCIAL EXPANSION · COMPLEX MARKETS

SELECTED MANDATES

REPRESENTATIVE EXPERIENCE ACROSS CAPITAL, M&A, AND COMMERCIAL ORIGINATION.

REPRESENTATIVE EXPERIENCE ACROSS CAPITAL, M&A, AND COMMERCIAL ORIGINATION.

REPRESENTATIVE EXPERIENCE ACROSS CAPITAL, M&A, AND COMMERCIAL ORIGINATION.

Selected engagements demonstrating how Breakout supports companies and sponsors through positioning, origination, and execution.

Selected engagements demonstrating how Breakout supports companies and sponsors through positioning, origination, and execution.

SELECTED MANDATES

Selected mandates across our team.

01 / 07
CAPITAL ADVISORY · ENTERPRISE AI
THE PROMPT GROUP

SEED ROUND FUNDRAISING COMPLETED IN UNDER 90 DAYS.

Breakout positioned the financing opportunity, identified aligned investors, and coordinated the process from market outreach through closing.

SEED ROUND COMPLETED · UNDER 90 DAYS · STRATEGIC INVESTOR ALIGNMENT
COMMERCIAL ADVISORY · LOGISTICS TECHNOLOGY
OCTUP

COMMERCIAL ORIGINATION VALIDATES A NEW 3PL MARKET CHANNEL.

Breakout tested positioning across multiple buyer profiles, identified stronger market alignment within the 3PL ecosystem, and executed the resulting origination program.

60+ DEMOS · $120K IN NEW ARR · REPEATABLE 3PL CHANNEL VALIDATED
M&A ADVISORY · BUY-SIDE ORIGINATION
PRIVATE EQUITY SPONSOR

THESIS-ALIGNED ACQUISITION PIPELINE FOR A VERTICAL SOFTWARE MANDATE.

Breakout translated the sponsor’s investment thesis into executable acquisition criteria, mapped and prioritized relevant businesses, and initiated direct founder engagement.

60+ FOUNDER CONVERSATIONS · PRIORITY US$30M ACQUISITION TARGET IDENTIFIED
M&A ADVISORY · TECHNOLOGY SERVICES
ATTCO GLOBAL SERVICES

~$50 MILLION TECHNOLOGY-AS-A-SERVICE ACQUISITION.

Acquisition of a technology-as-a-service platform within the broader technology-services market.

~$50 MILLION · ACQUISITION · TECHNOLOGY-AS-A-SERVICE
M&A ADVISORY · LOGISTICS & FULFILLMENT
NEOPOST

~$38 MILLION MAJORITY INVESTMENT.

Majority investment in a logistics and fulfillment platform operating across complex commercial markets.

~$38 MILLION · MAJORITY INVESTMENT · LOGISTICS & FULFILLMENT
COMMERCIAL ADVISORY · BUSINESS DEVELOPMENT FIRM
EXPLODING LEADS

28 QUALIFIED MEETINGS AND TWO NEW CUSTOMERS GENERATED IN 40 DAYS.

Breakout supported a focused commercial-origination mandate designed to expand qualified pipeline and convert outreach into new customer relationships.

28 MEETINGS · 2 NEW CUSTOMERS · 40 DAYS
COMMERCIAL ADVISORY · AI-ENABLED GROWTH TECHNOLOGY
DITTTO.AI

$150K IN NEW ARR ADDED THROUGH A FOCUSED COMMERCIAL ORIGINATION MANDATE.

Breakout refined the company’s commercial positioning and executed a targeted origination program to establish qualified pipeline and accelerate customer acquisition.

33 MEETINGS · $150K IN NEW ARR · 2.5 MONTHS

60+

Years combined advisory experience

$18B+

In aggregate transaction volume

2500+

Investor relations supported

Our Team

Terence Kawaja

Strategic Advisor

Terence Kawaja is the Founder and CEO of LUMA Partners, a strategic advisory firm at the intersection of media and technology. A seasoned investment banker with over two decades of experience, Terry has advised on more than $300 billion in transactions - including some of the most consequential deals in media and tech history. Prior to LUMA, he served as Global Head of Media M&A at Citigroup and Credit Suisse First Boston. He holds an MBA from the Schulich School of Business, a JD from Osgoode Hall Law School. 

Rana DiOrio

Strategic Advisor

Rana DiOrio is a technology investment banker, former corporate and securities attorney, entrepreneur, and investor whose career includes Merrill Lynch, Alex. Brown & Sons, Bank of America Securities, and North Point Mergers & Acquisitions, where she has served as Managing Director. Rana brings experience helping companies raise capital, pursue acquisitions, and develop and execute growth strategies. Her background combines software and technology investment banking with corporate and securities law experience at Wilson Sonsini Goodrich & Rosati and Pillsbury Madison & Sutro.

Darko Atijas

Strategic Advisor

Darko Atijas is a global operator and dealmaker whose career spans more than two decades across private equity real estate, venture-backed technology, and corporate finance. During his tenure in private equity, Darko contributed to several landmark transactions - including the $1.9 billion XI / 76 Eleventh Avenue mixed-use development in New York City featuring the Six Senses Hotel & Residences, and a $1+ billion portfolio of residential and hospitality projects across the U.S. and Europe.  He currently serves as COO of Tech Universal Ventures and holds board positions across emerging technology companies globally. He holds an MBA from Macquarie University.

About the Founder

Ryan Bryden

Founder

Ryan Bryden began his career in business development, learning firsthand how institutional relationships are formed and where distribution consistently breaks down. While still completing his Bachelor of Business Management at Western University, he founded Breakout Capital Group - an advisory firm built to solve the distribution problem for growth-stage companies struggling to build systematic sales pipeline through technology-enabled distribution.

The pattern he encountered in growth advisory kept surfacing in an unexpected place. The companies Breakout worked with weren't just struggling to find customers - they were struggling to find capital. And the investment banking infrastructure meant to solve that problem was operating on the same broken model: closed networks, static lists, and a process built around the advisor's relationships rather than the founder's outcome.

Bryden recognized the problem was identical. 

He partnered with a team of senior capital markets professionals - dealmakers with decades of transactional experience across Wall Street and boutique investment banking - and extended Breakout's origination methodology into the fundraising mandate. The result is a firm that brings institutional-grade advisory discipline and modern, data-driven origination infrastructure to the capital raise - working today with some of the world's best technology companies to deliver the access, precision, and timeline in a new age of investment banking and capital markets outcomes.

Breakout Capital Group is a capital advisory firm and is not a registered broker-dealer.
Any activity involving the offer or sale of securities is conducted solely through registered dealers, including in the United States in reliance on Rule 15a-6 under the Securities Exchange Act of 1934, and in accordance with applicable Canadian and U.S. securities laws. This website is for informational purposes only and is not an offer or solicitation to buy or sell any securities

Breakout Capital Group is a capital advisory firm and is not a registered broker-dealer.
Any activity involving the offer or sale of securities is conducted solely through registered dealers, including in the United States in reliance on Rule 15a-6 under the Securities Exchange Act of 1934, and in accordance with applicable Canadian and U.S. securities laws. This website is for informational purposes only and is not an offer or solicitation to buy or sell any securities

Breakout Capital Group is a capital advisory firm and is not a registered broker-dealer.
Any activity involving the offer or sale of securities is conducted solely through registered dealers, including in the United States in reliance on Rule 15a-6 under the Securities Exchange Act of 1934, and in accordance with applicable Canadian and U.S. securities laws. This website is for informational purposes only and is not an offer or solicitation to buy or sell any securities