Today on Digital Doorways, we’re joined by Eric Chase, a partner at CSP Associates—one of the most respected commercial diligence advisory firms serving the aerospace, defense, and government services sectors. CSP is the firm private equity turns to when precision matters most—when understanding market dynamics, customer traction, competitive moats, and future growth levers can mean the difference between a winning investment and a costly misread. With decades of experience and deep industry roots, Eric has advised on hundreds of transactions, shaping the strategies behind some of the most impactful investments in the national security ecosystem.
In this conversation, we’ll dive into how branding and marketing—often underappreciated in diligence—are increasingly central to how companies manage risk, accelerate growth, and navigate shifting market dynamics. From repositioning legacy contractors in evolving threat environments to helping tech-first entrants earn trust in the federal space, Eric shares how CSP is seeing value creation change. We’ll explore what defines a standout brand in GovCon today, how sponsors should think about commercial levers post-close, and why the story you tell might be as important as the contracts you win.
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1. What role does branding and market positioning play in commercial diligence, especially in GovCon or A&D sectors?
2. How have you seen marketing strategy evolve as a factor in private equity decision-making?
3. Can a strong brand meaningfully impact valuation or exit strategy in these traditionally relationship-driven markets?
4. When evaluating a target, how do you assess the strength—or weakness—of its brand?
5. What are the red flags you see when companies fail to align their messaging with market realities?
6. Are there examples where branding or go-to-market repositioning significantly unlocked growth post-investment?
7. How does CSP evaluate customer perception in the diligence process? Do you measure “brand trust” or awareness?
8. In defense and national security, trust and credibility are everything. How does that intersect with marketing?
9. How can legacy firms modernize their brand without losing what made them credible in the first place?
10. What do sponsors often underestimate about the power of storytelling when entering federal or aerospace markets?
11. How should founders and leadership teams think about branding as part of their pre-exit strategy?
12. In dual-use tech or defense-tech ventures, how do companies balance commercial appeal with mission-first branding?
13. What are the key marketing differentiators between average and great companies in your diligence work?
14. As AI and autonomy reshape the landscape, how are the most compelling companies framing their narrative?
15. Can branding help smooth transitions during roll-ups, carve-outs, or rebranding after an acquisition?
16. How early in the process do you recommend a company begin investing in its brand if a transaction is on the horizon?
17. Do you see differences in how branding is valued between strategic acquirers and private equity buyers?
18. What advice would you give to growth-stage companies trying to stand out in crowded federal sectors?
19. How do you see the role of commercial marketing teams evolving inside traditionally engineering-driven organizations?
20. Finally, what’s one brand or repositioning you’ve seen in the defense or GovCon space that really impressed you?

Today on Digital Doorways, we’re spotlighting a leader who’s built his company not on flash, but on focus. Boladji Agueh, CEO of Squadra Solutions, has taken a scrappy, adaptive approach to building one of the most talked-about emerging brands in the space. With no glossy campaigns or high-end branding playbook, Squadra has instead earned attention by solving hard problems, reacting in real time to customer demands, and staying razor-sharp in the face of technological change.

In an era defined by AI disruption, shifting client expectations, and a noisy digital landscape, Boladji has stayed relevant by leaning into agility, trust, and innovation. Now, with Squadra’s major partnership with Georgetown University, the company is stepping onto an even bigger stage. Today, we unpack how Boladji thinks about change, relevance, and what it really takes to build in public—without the usual safety nets.

QUESTIONS INCLUDE:

• What’s a moment in Squadra’s journey when you had to quickly pivot or rethink everything?

• How do you build a team and culture that stays nimble in the face of evolving client needs?

• What role does experimentation play in how you run the business?

• How has AI changed the expectations of your customers or partners?

• What are you doing to keep Squadra relevant and competitive as AI accelerates across industries?

• Are you embracing AI in your own internal operations, or more on the client side first?

• Squadra has grown without the typical bells and whistles of a polished brand. Was that intentional—or just the reality of building lean?

• What has helped you gain trust from large partners like Georgetown without a high-end marketing engine?

• Looking ahead, how do you think about investing in brand as a lever for growth?

• Tell us about the Georgetown partnership—what made the timing and alignment right?

• How do you approach big institutional partnerships when you’re still scaling?

• What does success look like beyond the contract—what’s the broader impact you’re hoping for?

• What’s your “why” right now? Has it changed since you started Squadra?

• What does the next stage of growth look like—and what will you need to do differently to get there?

• If Squadra is front and center in a major headline five years from now, what would you want it to say?

Today’s guest is Steve Feldman, the visionary Founder behind Private Prep — one of the country’s most exciting education brands. What began as a local tutoring service out of Steve’s New York City apartment has evolved into a multi-dimensional organization that works with studnets all over the country and world, now spanning academic tutoring, test prep, and college admissions coaching and consulting. In an industry where trust, expertise, and adaptability are everything, Steve has successfully repositioned Private Prep to stay ahead of changing student needs and parental expectations — while building a brand that competes and wins on experience, personalization, and proven outcomes. In today’s conversation, we’ll explore how he’s navigated that transformation, how brand positioning fuels Private Prep’s growth, and what other businesses can learn about staying relevant in fast-evolving markets.