Opportunistic and Niche Direct Credit
Senior secured lending to the lower-to-middle market segment
An all-weather opportunistic private credit strategy, focused on the lower middle market segment. We seek to capitalize on North American investment opportunities that are time-sensitive, complex, or in dislocated markets where we believe risk is fundamentally mispriced.
The strategy’s core qualities:
- Senior secured lending at the top of the capital structure.
- Strict loan covenants through various forms of guarantees, payment restrictions, and financial metrics.
- Seeks additional upside with equity kickers and/or exit fees.
This strategy focuses on liquidity solutions, growth and technology finance, loans to esoteric industries, and specialty asset-based loans.
$M
TARGET LOAN SIZE
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SENIOR SECURED
AVERAGE LOAN DURATION (MONTHS)
Fund III Overview
Lending Verticals
We seek to provide senior secured financing to smaller companies in the lower to middle market segment with the following qualities, in the following verticals.
Specialized Industries
- Regulatory, reputational or other risks
- Minimally-levered operators with strong cash flows
- Warrants/equity kickers & favorably priced
Liquidity Solutions
- Borrowers experiencing a liquidity event or in need of driving financing (merger, dividend recap)
- Lower leverage, higher collateral
- GP/NAV based loans
Growth & Technology
- Industry leaders/disruptors, seeking to drive exponential growth
- Sectors from software to hardware to e-commerce
- Lower debt to enterprise value, with a path to profitability

Our Differentiators
We play in the “corners of the market”, where intensive due diligence is a must – and where competitive pressures often preclude other traditional lenders from participating.
Fortunately, we are fastidious underwriters who think multi-dimensionally, pairing our management expertise with tailored covenants to create a mutually beneficial product that drives our borrowers’ strategic growth, and seeks to results for investors.
Our Approach to Risk Management
Meet the Team
Tony CappellPartner
- All partners sit on the Investment Committee, but Tony takes a lead on the day-to-day running of this strategy.
- Experienced debt investor with over 15 years of specialty finance experience.
Tony CappellPartner
Tony Cappell is a Partner & Co-founder at Chicago Atlantic. As a debt investor with over 15 years of experience in the specialty finance space, Tony has completed over 150 deals comprising over $5B in total credit. Prior to founding Chicago Atlantic, Tony was a Managing Director and Head of Underwriting at Stonegate Capital, a private credit investment firm focused on lower middle market businesses and emerging brands. At Stonegate, he was responsible for credit, underwriting and the growth strategy of the loan portfolio. Previously, he was a Senior Underwriter at First Midwest Bank and at Gibraltar Business Capital where he worked on a number of specialty finance transactions including technology, software, turnaround/distressed and re-discount loans. He began his career at Wells Fargo Capital Finance focused on a wide array of industries and loan structures.
MBA, The University of Chicago Booth School of Business
BA, University of Wisconsin, Milwaukee
David EnrightPartner, Head of Direct Lending
- Senior leader for Fund III, responsible for go-to-market strategy, raising capital, hiring talent, and helping with internal processes, procedures and policy.
- A debt investor with over 23 years of experience in specialty finance.
David EnrightPartner, Head of Direct Lending
As a debt investor with over 21 years of experience in the specialty finance space, David has completed over 300 deals comprising over $7.5 billion in total credit. Prior to joining Chicago Atlantic, David was an SVP responsible for the strategy of Specialty Finance and C&I lending at S&T Bank (NASDAQ: STBA). Previously, he was National Head of Sales at First Midwest Bank and co-founder of Specialty Finance for First Financial Business Capital, a division of First Financial Bank. While at both First Midwest and First Financial Business Capital, David worked on a number of specialty finance transactions including mezzanine loans, unitranche in almost every industry sector, asset-based lending, technology, software, turnaround, rediscount and many more. He began his career at National City Bank focused on a wide array of industries and loan structures.
BA (Economics), Kenyon College
Dino Colonna, CFA®Partner, Originations
- Responsible for the origination, diligence, and execution of investments.
- 20+ years of experience across alternative investments and investment banking, with a focus on investing across public and private credit strategies, and a track record of navigating multiple credit cycles.
Dino Colonna, CFA®Partner, Originations
Dino is a Partner at Chicago Atlantic focused on originations. Since 2001, Dino has managed traditional and alternative investment portfolios and advised corporations and institutional investors across the global capital markets.
Prior to Chicago Atlantic, Dino was managing partner at Madison Capital Advisors, a middle-market asset-backed lending and advisory firm focused on emerging growth companies in the cannabis, life sciences and tech sectors. Prior to Madison, Dino spent over 10 years as an investment banker at the top-ranked Equity Capital Markets team at Barclays in London, and as a senior research analyst at Forest Investment Management, a global multi-strategy hedge fund. With Barclays, he advised on and structured over $8bn of equity, derivative and debt transactions and while at Forest, he specialized in credit and equity research and was part of the portfolio management team managing a $500mm+ multi-strategy portfolio.
MBA (Finance and Entrepreneurship), Esade
BS (Major: Finance, Minor: Economics), University of Delaware
CFA® charterholder, CFA Institute
Jack FlahertyManaging Director, Credit
- Senior advisor for Fund III.
- Jack’s experience spans high-yield, investment-grade and emerging markets investing, covering structured credit, asset-backed and mortgage-backed credits, trade finance, opportunistic lending strategies and insurance-linked securities.
Jack FlahertyManaging Director, Credit
Jack joins after 14 years at GAM in New York City as Investment Director and co-head of credit strategies firmwide and also was co-manager of GAM’s unconstrained/absolute return bond strategy responsible for credit positions ranging from investment grade to high yield debt including both asset-backed and mortgage-backed securities allocations. In addition, he has extensive experience in structured credit, trade finance, lending strategies and insurance linked securities. He was previously global co-head of credit fixed income and global head of emerging markets at UBS and worked as a managing director at Barclays Capital in charge of credit fixed income.
Jack Flaherty holds the Series 7, 63 and 24 qualifications. He is currently living in Los Angeles.
MBA (Finance and Accounting), University of Chicago
BA (Economics), University of Illinois
Tim AndersonManaging Director, Institutional Business Development
- Responsible for bringing Chicago Atlantic’s private market solutions to institutional investors, family offices and consultants.
- 20+ years as an institutional fundraiser, focused on endowments/foundations, family offices, pensions and consultants.
Tim AndersonManaging Director, Institutional Business Development
With twenty-four years’ experience in the alternatives space, Tim has successfully raised over $3 billion in capital for multi-strategy hedge funds, credit funds and a family office anchored real estate fund. He most recently served as Managing Director at Marquee Capital, a real estate firm within the Marcus Family Office, where he institutionalized the investor relations program. Tim’s career also includes tenures at Stark Investments, Trian Credit Partners, 3i Capital, Macquarie and One William Street Capital Management.
With relationships across the allocator universe, Tim has worked to raise capital with endowments & foundations, consultants, family offices, pensions, and wealth managers alike. He presently leads Chicago Atlantic’s institutional fundraising efforts.
MBA (Finance, Investments & Banking), University of Wisconsin-Madison
BA, Vanderbilt University
Kushal Kshirsagar, Ph.D.Managing Director, Private Wealth Solutions
- Responsible for bringing Chicago Atlantic’s private market solutions to individual investors and their advisors.
- 20+ years experience as an investment advisor to asset owners and their fiduciaries (CIOs, CFOs, investment committees, and treasurers).
Kushal Kshirsagar, Ph.D.Managing Director, Private Wealth Solutions
Kushal serves as Managing Director, Private Wealth Solutions and is responsible for bringing Chicago Atlantic’s private market solutions to individual investors and their advisors.
Prior to joining Chicago Atlantic, Kushal worked for BlackRock for over a decade in San Francisco, New York and Singapore. He served various roles in BlackRock’s Multi-Asset Strategies, US Wealth Advisory and iShares divisions, spanning investment research, portfolio management, portfolio strategy and business development.
Previously, he was a Director at UBS in London and New York where he designed recapitalization strategies for banks, insurance and reinsurance companies. Prior to that, as a Vice President at Credit Suisse in New York, Kushal developed financing solutions for public and PE-owned energy, healthcare and technology companies. Kushal began his career at the Vanguard Group where he developed investment solutions for pension plans, endowments and foundations and was the principal architect of Vanguard’s Capital Markets Model.
Ph.D (Finance), The University of North Carolina at Chapel Hill
Michael TrompeterDirector, Growth & Technology Finance
- Responsible for originating and structuring deals within the tech and growth finance strategy.
- Over 8 years of experience in technology finance and venture debt.
Michael TrompeterDirector, Growth & Technology Finance
Michael Trompeter is a Director of Growth & Technology Finance at Chicago Atlantic. He is responsible for the origination and execution of investments on the Direct Lending team. Prior to joining Chicago Atlantic, he was a Senior Associate at Golub Growth, where he invested across the capital structure and was responsible for originating, screening and diligence of late-stage enterprise software investments. During this time, Golub Growth deployed over $1 billion into late-stage enterprise software companies. Prior to his work with Golub, Michael worked at Waud Capital Partners on the business development team, sourcing platform and add-on opportunities for the multi-billion dollar private equity firm.
BS (Finance), Illinois State University
Colin Cordes, CFA®Director, Underwriting & Portfolio Management
- Responsible for deal structuring, underwriting, and portfolio management of private debt investments.
- Over 12 years of experience in various credit roles.
Colin Cordes, CFA®Director, Underwriting & Portfolio Management
Colin is a Director of Underwriting & Portfolio Management at Chicago Atlantic. He is responsible for the underwriting process for new investments including due diligence, financial modeling and risk assessment. Additionally, he oversees the performance and risk management of existing portfolios within the Direct Lending team, while also assisting with funding and operating procedures.
Prior to joining Chicago Atlantic, Colin was a Senior Credit Analyst at Macquarie Asset Management and AMP Capital where he specialized in the Energy sector for the Global Infrastructure Bond Fund. His career includes experience as a credit analyst at Fitch Ratings and a trader at Geneva Trading.
BA (Economics), Princeton University
CFA® charterholder, CFA Institute
Evan BuckwalterVice President, Esoteric & Liquidity Solutions
- Responsible for sourcing, structuring, and executing finance opportunities.
- More than 6 years of experience in direct lending and credit investment.
Evan BuckwalterVice President, Esoteric & Liquidity Solutions
Evan serves as Vice President of Esoteric and Liquidity Solutions at Chicago Atlantic, where he is responsible for sourcing, structuring, and executing finance opportunities within the group’s direct lending strategy. He is based in the firm’s New York City office.
Evan has more than six years of experience in direct lending and credit investment. Prior to joining Chicago Atlantic, Evan was a Senior Associate at Colbeck Capital Management, a Private Credit Fund focused on middle-market opportunistic credit. At Colbeck, Evan helped deploy over $275 million in closed credit facilities across industries including logistics, financial services, multi-unit businesses, insurance, and renewable energy.
Earlier in his career, he held business development roles at start-up fintech firms and in the structured settlement space.
MSc (Business), University of Nottingham
BA (Economics), Occidental College
Michael OrlandoVice President, Growth & Technology Finance
- Responsible for the origination, diligence, and execution of investments
- Over 10 years of varied investment management experience
Michael OrlandoVice President, Growth & Technology Finance
Michael services as a Vice President of Growth & Technology Finance at Chicago Atlantic. He joins from ATEL Ventures, a division of ATEL Capital Group where he most recently served as a Vice President of their Originations Team. Prior to ATEL Michael previously held roles at companies including Bridge Bank (Division of Western Alliance), Square 1 Bank (a division of Pacific Western Bank, now Bank of California) and BNY Wealth Management.
Active in the San Francisco community, Michael is a Board Member of Opportunity for Independence OFI, an organization helping to enhance the quality of life for individuals with developmental and other cognitive disabilities throughout Marin County.
BS (Business Administration), University of Southern Maine
Luis CardenasSenior Associate, Underwriting & Portfolio Management
- Supporting all aspects of the investment process including underwriting, originating, and portfolio management.
Luis CardenasSenior Associate, Underwriting & Portfolio Management
Luis is a Senior Associate on the Underwriting & Portfolio Management team at Chicago Atlantic focusing on supporting all aspects of the investment process including underwriting, originating, and portfolio management. Prior to joining Chicago Atlantic, Luis worked as an Investment Banking Analyst in the Mergers & Acquisitions group at BMO Capital Markets.
BS (Finance), University of Illinois at Urbana-Champaign
Nick HongAssociate, Underwriting & Portfolio Management
- Supports aspects of the investment process across underwriting, originations, and portfolio management.
Nick HongAssociate, Underwriting & Portfolio Management
Nick is an Associate of Underwriting and Portfolio Management at Chicago Atlantic, where he supports the firm’s investment process across origination, underwriting, and portfolio management. Within the firm’s direct lending strategy, he covers sectors including Growth & Technology Finance, Liquidity Solutions, and Esoteric industries. Prior to joining Chicago Atlantic, Nick was an Analyst at J.P. Morgan on their Syndicated Finance desk. During this time, he helped the team reach a milestone of 500 Lead Left syndicated transactions.
BA (Economics), Kenyon College
Tyler EhrmanAnalyst, Underwriting & Portfolio Management
- Supports aspects of the investment process across underwriting, originations, and portfolio management.
Tyler EhrmanAnalyst, Underwriting & Portfolio Management
Tyler is an Underwriting Analyst at Chicago Atlantic. He supports the underwriting process for new investments. Prior to joining Chicago Atlantic, Tyler completed internships at Consensus, T-Mobile, and Encompass Capital.
BS (Finance and Business Analytics), University of Miami
Lila HuddlesAnalyst, Investor Relations
- Supports all aspects of investor relations.
Lila HuddlesAnalyst, Investor Relations
Lila is an Investor Relations Analyst at Chicago Atlantic. Prior to joining the team, Lila completed an internship with Chicago Atlantic, where she worked with the Underwriting team. Lila recently graduated from Vanderbilt University in Nashville, TN, and was a four-year member of the Women’s Division I Lacrosse team.
BS (Human and Organizational Development/Business), Vanderbilt University
