PE Family Offices With Warm Intros to DeepSignal via St Cloud, RLH Equity, Century Park

Executive Summary

This report identifies direct, warm-introduction pathways to specific private equity (PE) firms and family offices to secure a Proof of Concept (POC) for DeepSignal ahead of the March 19, 2026, ACG Middle-Market AI Demo Day. Based on co-investment history, shared portfolio data, and verified professional networks, the research yields the following actionable findings:

Primary Deal-Leader Targets: The most direct pathways exist via Gallant Capital Partners, Shamrock Capital, The Riverside Company, and RLH Equity Partners.
Key Relationship Nodes: Matt Smith (St. Cloud Capital), Ryan Smiley (Shamrock Capital / formerly RLH), and Matt Minnaugh (Century Park Capital) share highly documented intersections, specifically via the ACG 101 chapter and the UCLA Anderson School of Management ^[3], ^[7].
Optimal DeepSignal Angles: Target origination and business development leaders (like Matt Minnaugh and Jeremy Holland) by positioning DeepSignal as a competitive equalizer, utilizing RLH’s recent $100M strategic investment in AI-driven Keystone Strategy ^[2], ^[18] as a compelling industry benchmark.

1. Confirmed PE Targets and Overlapping Portfolios

To effectively penetrate the target demographic, DeepSignal must leverage existing co-investments and established ecosystem overlaps. The following firms present the highest probability of conversion based on their direct ties to the specified relationship nodes:

Gallant Capital Partners

Relationship Node: St. Cloud Capital (Matt Smith)
Overlap Details: Gallant Capital Partners shares a direct co-investment history with St. Cloud Capital in the portfolio company Business Processing Solutions, LLC (BPS) ^[1].
Key Target: Anthony Guagliano, Partner at Gallant Capital ^[17]. Kacy Rozelle (Managing Partner at St. Cloud) has publicly collaborated with Guagliano on this growth capital investment ^[1], ^[17].
Firm Context: St. Cloud Capital operates closely in this tier, having managed over $700M since 2001 ^[13] and recently deploying capital from its $236M fourth fund ^[5]. This establishes St. Cloud as a highly credible introducer to Gallant.

Shamrock Capital (The Clover Fund)

Relationship Node: Ryan Smiley
Overlap Details: Ryan Smiley, who spent over 15 years as a General Partner and Managing Director at RLH Equity Partners ^[4], is now a Partner at Shamrock Capital’s Clover Fund ^[8]. Smiley has deep roots at Shamrock, having previously worked there as an Associate earlier in his career (following a stint at Bear Stearns) ^[16], ^[20].
Key Target: Ryan Smiley himself, given his operational oversight as a director for portfolio companies CardsHQ, Mutiny, and Neocol ^[12].

The Riverside Company

Relationship Node: Shared ACG 101 Ecosystem (Matt Minnaugh, Matt Smith, Ryan Smiley)
Overlap Details: Jeremy Holland serves as Managing Partner at The Riverside Company, leading the North American origination team across various funds and strategies ^[15]. Holland established a direct professional tie with Matt Minnaugh (Century Park), Matt Smith (St. Cloud), and Ryan Smiley (RLH) by co-paneling an ACG 101 M&A and Private Equity event ^[7].
Firm Context: While Riverside manages approximately $13B in AUM ^[19] (exceeding the strict $200M–$2B criteria), their dedicated middle-market focus and Holland’s direct responsibility for deal origination make them an ideal candidate for an AI sourcing tool like DeepSignal.

RLH Equity Partners

Relationship Node: Ryan Smiley (Legacy) & Matt Smith (Alumni network)
Overlap Details: RLH targets knowledge-based enterprises with up to $200M in annual revenue ^[6], typically utilizing recapitalization structures ^[21]. They operate in business services, healthcare, and government services ^[10], ^[24].
Key Target: Chris Lewis, Co-Founder and Managing Director ^[14]. RLH recently completed a $100M strategic investment in Keystone Strategy ^[2], a firm specializing in AI-driven digital transformation ^[18].

2. Professional Ties and the Deal-Leader Matrix

The successful deployment of a warm-introduction strategy relies on understanding the exact nature of the professional ties between the target contacts.

Target Leader	Current Firm	Role/Focus	Relationship to Smith / Smiley / Minnaugh
Anthony Guagliano	Gallant Capital Partners	Partner	Co-investor with St. Cloud Capital (Matt Smith's firm) on BPS ^[1], ^[17].
Ryan Smiley	Shamrock Capital	Partner, Clover Fund	Direct Node: Fellow UCLA Anderson MBA alumnus with Matt Smith ^[3], ^[23]. Co-panelist at ACG 101 with Smith and Minnaugh ^[7].
Jeremy Holland	The Riverside Company	Managing Partner, NA Origination	Co-panelist at ACG 101 event with Minnaugh, Smith, and Smiley ^[7], ^[15].
Chris Lewis	RLH Equity Partners	Co-Founder & MD	Former colleague/managing partner of Ryan Smiley (Smiley was GP at RLH for 15+ years) ^[4], ^[14].
Matt Minnaugh	Century Park Capital Partners	Director of Business Development	Direct Node: Responsible for BD and deal sourcing efforts ^[11]. Shared ACG 101 panel with Smith, Smiley, and Holland ^[7].

Alumni and Historical Ties

Matt Smith (who previously founded the Structured Finance Group at Banc of California ^[22] and acts as St. Cloud's Media Contact ^[9]) and Ryan Smiley share a highly actionable educational tie: both earned their MBAs from the UCLA Anderson School of Management ^[3]. Smiley specifically attended as a Venture Fellow ^[23].

3. Recommended Outreach Sequence & Messaging Angle

To secure a DeepSignal POC before the March 19, 2026 ACG Middle-Market AI Demo Day, outreach must be sequenced to leverage the strongest collegiate and shared-investment ties first, utilizing highly specific AI-driven value propositions.

Phase 1: Activate the Anderson / ACG Alliance (Months 1-2)

Target: Ryan Smiley (Shamrock) and Matt Smith (St. Cloud).
Messaging Angle: Approach Smiley via his shared UCLA Anderson background with Smith ^[3]. Position DeepSignal not as a generic vendor, but as a portfolio-value-creation tool for his board seats at CardsHQ, Mutiny, and Neocol ^[12].
Ask: Secure Smiley as an internal champion to provide feedback on DeepSignal’s viability for knowledge-based middle-market enterprises, leveraging his 15+ years of experience targeting that exact demographic at RLH ^[4], ^[24].

Phase 2: Target the Origination Leaders (Months 3-4)

Target: Matt Minnaugh (Century Park) and Jeremy Holland (Riverside).
Messaging Angle: Both leaders are actively responsible for deal sourcing and business development ^[11], ^[15]. Utilize their shared history from the ACG 101 panel ^[7] to orchestrate a joint "Origination Innovation" briefing.
Value Proposition: Reference RLH’s recent $100M investment into Keystone Strategy ^[2], highlighting Keystone's focus on "AI-driven digital transformation" ^[18]. Message to Minnaugh and Holland that while their peers are investing in AI consultancies, DeepSignal offers an immediate, deployable AI transformation for their own internal deal-sourcing pipelines.

Phase 3: The Co-Investor Network Conversion (Months 5-6)

Target: Anthony Guagliano (Gallant Capital).
Messaging Angle: Utilize Kacy Rozelle or Matt Smith at St. Cloud Capital ^[1], ^[9] to broker an introduction to Guagliano. The messaging should focus on operational efficiencies at co-owned portfolio companies like BPS ^[1], ^[17], proposing a DeepSignal POC as a mutual value-add to accelerate BPS's next growth stage before the 2026 ACG Demo Day.

4. Limitations and Open Questions

While the evidence provides strong pathways, several gaps remain that require further primary research:

Fund Size Validation: The provided data does not confirm the exact current AUM for Gallant Capital Partners or Century Park Capital Partners, making it unclear if they strictly fall within the $200M–$2B AUM target bracket. (St. Cloud's historical management of >$700M ^[13] and RLH's target parameters ^[6] fit the criteria well).
Riverside AUM Constraint: The Riverside Company manages ~$13B ^[19], vastly exceeding the $200M–$2B AUM cap. Outreach to Jeremy Holland must be calibrated to recognize this scale.
Current Tech Stacks: There is no documented visibility into the existing CRM or deal-sourcing software currently utilized by Gallant, RLH, or Shamrock, which is necessary to finalize the technical integration requirements for a DeepSignal POC.

Sources