Welcome to Digital Doorways, the podcast where we explore how visionary leaders are transforming business through creativity, technology, and growth. I’m Jason Siegel, founder of Bluetext, and today we’re joined by a world-renowned marketing innovator who’s redefining how companies think about outbound growth and digital engagement. From New York to Da Nang, Vietnam, he’s built an international reputation for crafting systems that turn outreach into measurable, scalable revenue. As the co-founder of Revenue Boost, his work has been featured by Digital Marketer, Adworld, Foundr Magazine, The Futur, and Outbound Squad — cementing his place among the top thinkers in modern sales and marketing strategy, and how to use AI to increase revenue

We’ll unpack his journey from managing a 20-person sales team in his early twenties to leading a global B2B outreach firm and consultancy that’s reshaping how businesses grow in today’s competitive landscape. He’s more than a sales expert — he’s a strategist, a teacher, and a relentless optimist about the power of persistence and connection. This is a conversation about precision, process, and the mindset required to turn every opportunity into revenue — on this episode of Digital Doorways.

QUESTIONS INCLUDE....

How has the philosophy of lead generation evolved over the past few years — and what changes have had the biggest impact on your playbook?

In a world of automation and AI, how do you maintain authenticity in outbound email and LinkedIn campaigns?

What’s the most underrated signal that tells you a lead is ready to convert?

How do you balance volume versus precision when running LinkedIn and email campaigns for B2B audiences?

Can you share an example of a small tweak in messaging or positioning that dramatically improved conversion rates?

How do you adapt your outreach strategies when major changes hit — whether that’s a platform algorithm shift, new privacy regulation, or an internal brand repositioning?

When you’re brought into a company going through transformation, what’s your first step in aligning their lead generation strategy with the new brand story?

What lessons have you learned about leading marketing teams through change without losing momentum?

How do you handle the tension between short-term lead goals and long-term brand equity during times of transition?

Is there a campaign or client where managing change became the key factor in success?

How do you translate brand positioning into actionable lead-generation messaging?

What’s your process for turning a brand narrative into a compelling LinkedIn outreach sequence?

When rebranding or repositioning, how should companies rethink their prospecting lists and messaging tone?

How important is thought leadership in shaping a brand’s ability to generate inbound leads today?

What’s the role of emotional storytelling in an era where metrics and automation dominate?

What emerging tools or trends in LinkedIn or email outreach excite you the most right now?

Where do you think personalization ends and intrusion begins?

If you could redesign the modern lead funnel for today’s hybrid buyer journey, what would it look like?

How do you measure success beyond open and click rates — what tells you your brand is actually resonating?

Finally, when the dust of change settles, what remains timeless about connecting with another human through marketing?

Welcome back to Digital Doorways. I’m Jason Siegel, founder of Bluetext, and your host for conversations with leaders who are redefining industries through brand, technology, and transformation.Today I’m joined by Sam Meek, CEO and co-founder of Sandboxx. Sam has built one of the most innovative platforms in the military community — a digital ecosystem that connects service members, families, and veterans through technology, storytelling, and support.From reimagining how recruits and their loved ones stay connected during basic training, to expanding into media and services that shape the broader defense community, Sam has led Sandboxx through rapid growth, cultural change, and evolving digital strategies.In this conversation, we’ll explore how Sam has navigated change, leveraged brand and positioning to build trust in a mission-critical space, and used digital marketing to scale impact.⸻Navigating Change & Growth 1. Sandboxx started as a way to connect recruits and families — how has the mission evolved since then? 2. What was the biggest moment of change in Sandboxx’s journey, and how did you navigate it? 3. How do you balance scaling a business with staying true to the military community’s core needs? 4. What’s the toughest pivot you’ve had to make as CEO?Brand & Positioning 5. Sandboxx operates in a trust-driven space. How did you establish credibility with service members and their families early on? 6. How do you position Sandboxx differently from traditional defense contractors or tech startups? 7. Can you share a moment where refining your positioning unlocked new opportunities? 8. What role does storytelling play in building the Sandboxx brand?Digital Marketing & Community 9. Sandboxx blends product with media. How do you think about digital marketing differently than a pure-play SaaS company? 10. What channels have been most effective in building awareness and engagement? 11. Sandboxx has over 30 million users and billions of impressions on YouTube — how do you harness that reach strategically? 12. How do you measure the ROI of community engagement compared to more traditional marketing metrics?Leadership & Culture 13. What’s unique about leading a company that serves both families and service members? 14. How do you keep your team motivated when the mission is so emotionally charged? 15. What leadership lessons have you taken from the military that you apply at Sandboxx? 16. How do you foster innovation inside a company that works with institutions known for hierarchy and tradition?Future of Sandboxx 17. Where do you see Sandboxx expanding next — media, technology, partnerships? 18. How do you envision Sandboxx shaping the broader defense and national security conversation? 19. What risks do you see ahead for Sandboxx as it continues to scale? 20. If you had one piece of advice for other CEOs building community-driven platforms, what would it be?

Welcome back to Digital Doorways. I’m Jason Siegel, founder of Bluetext, and your host for today’s conversation on how leaders navigate change in fast-moving industries.

Joining me is Marc Murphy, CEO of Ignite Digital Services. Marc has built a reputation as a transformative leader — from scaling Spark Consulting into a company acquired by Booz Allen Hamilton, to leading Ignite’s digital transformation work in the national security and defense sectors. Along the way, he’s been recognized as an EY Entrepreneur of the Year finalist and has championed a culture that earned Ignite a spot among the ‘Most Loved Workplaces.’

Marc’s career is a study in how brand, positioning, and digital strategy can be powerful levers for guiding organizations through disruption. Today, we’ll dig into the lessons he’s learned about building resilient brands, aligning teams through change, and turning transformation into opportunity.

QUESTIONS INCLUDE:

• You’ve led multiple organizations through major transformations. How do you personally define “change” in a business context?

• When disruption hits — whether technology, competition, or policy — what’s your first move as a leader?

• What was the biggest lesson you learned from scaling Spark Consulting so rapidly before its acquisition?

• How did that experience shape how you lead Ignite today?

• Many leaders treat brand as cosmetic. How do you see brand as a strategic tool for managing change?

• Can you share an example where a rebrand or repositioning helped an organization embrace transformation?

• How do you balance maintaining brand consistency with evolving for the future?

• In moments of uncertainty, how important is brand trust to clients, employees, and investors?

• Ignite operates in a crowded consulting market. How do you position the brand to stand apart?

• How does positioning shift when your clients are national security and mission-driven organizations?

• What’s the most common mistake you see companies make when repositioning during disruption?

• How do you differentiate between repositioning for survival versus repositioning for long-term growth?

• When industries are under pressure, do you see digital marketing as more of a defensive shield or an offensive weapon?

• What digital channels or tactics have proven most resilient during times of turbulence?

• How do you think AI is accelerating change in digital marketing?

• What metrics matter most when marketing through disruptive cycles — growth, resilience, or something else?

• You emphasize building a “Most Loved Workplace.” How do internal culture and brand connect in times of change?

• How do you keep your team engaged and confident when navigating disruption?

• What’s the hardest leadership lesson you’ve learned about managing through transformation?

• If you had to give one piece of advice to CEOs facing disruptive change today, what would it be?

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.
⸻
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.

Welcome to Digital Doorways, the podcast where we explore how visionary leaders drive transformation through bold strategy, brand thinking, and innovation. I’m your host, Jason Siegel, founder of Bluetext — an agency that helps growth-stage companies position themselves to win in moments of disruption. Today’s guest is someone who knows exactly what it means to lead through change. Pete Roney is the CEO of Detroit Defense, a newly formed company that was carved out of Ricardo Defense — a bold move that required not just operational expertise, but a sharp understanding of brand positioning in a complex, high-stakes industry.

In this conversation, we dig into how Pete approached the challenge of launching a new defense brand from a legacy business, how he used branding as a tool for internal alignment, and why positioning isn’t just about messaging — it’s about shaping perception during moments of uncertainty. From choosing the name Detroit Defense to crafting a narrative that speaks to both tradition and transformation, Pete brings a masterclass in how to use brand as a stabilizing and growth-driving force when the stakes are high. Let’s get into it.

QUESTIONS INCLUDE:

Company Origin & Strategic Positioning

• What inspired you to carve out Detroit Defense from Ricardo Defense, and how did you position the new brand in the marketplace from day one?

• When creating Detroit Defense, how did you define what the brand should stand for—especially in contrast to Ricardo Defense?

• How did you ensure continuity for existing clients while introducing a completely new brand identity?

• What role did the name Detroit Defense play in your positioning strategy? Why “Detroit”?

• How did you differentiate Detroit Defense in a space dominated by legacy defense contractors and rising tech-forward startups?

• What were some of the toughest internal conversations you had when communicating the brand shift to employees and partners?

• How did you use branding as a tool to align company culture during the transition?

• In the early days of the carve-out, how did you use internal comms to reinforce Detroit Defense’s new identity and mission?

• What lessons did you learn about change management that you didn’t expect when spinning out and rebranding?

• How important was transparency in building trust through the rebrand—and how did you execute it?

• How did customers react to the new Detroit Defense brand? Were there any misconceptions you had to address early on?

• What channels or messaging tactics were most effective in introducing the new brand to customers and stakeholders?

• How did you position Detroit Defense differently for government vs. commercial defense partners?

• What role does legacy—your past with Ricardo—play in Detroit Defense’s current messaging? Do you embrace or distance from it?

• Did you use any “anchor clients” or case studies to validate the new brand in the early stages?

• What was your approach to creating a visual identity that reflects the new company's values and strategic goals?

• How do you balance modern design with the traditional seriousness of the defense industry?

• Did you view brand development as a one-time launch or as an evolving process? How often do you revisit it?

• What’s the next big milestone for Detroit Defense, and how will branding help you get there?

• If you had to distill Detroit Defense’s brand into one sentence for a new recruit, what would it be?

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Welcome to Digital Doorways, where we explore the strategies, stories, and bold moves behind transformational change. I’m your host, Jason Siegel⁠, founder of Bluetext — a branding and marketing agency that helps high-growth companies win at moments of inflection. Today, I’m joined by an entrepreneur who’s proven that great innovation transcends industry. Sam Pollaro is a master builder — whether in hospitality, healthcare, or any vertical in between. From launching a hospitality CRM that was ultimately acquired by Booking.com and integrated into the OpenTable platform, to his latest venture at the intersection of care delivery and technology, Sam has a proven eye for solving big, complex problems.

As the co-founder and Co-CEO of PicassoMD, Sam is tackling one of the most urgent challenges in healthcare: enabling real-time collaboration between primary care physicians and specialists. Today, we’ll unpack how he spotted a powerful gap in the market, what it took to build trust in a complex industry, and how smart positioning and clear brand values can drive both adoption and impact. Whether you’re in tech, healthcare, or anything in between, this is a conversation about innovation under pressure — and how to win by staying focused on the people you serve.

QUESTIONS WILL INCLUDE....

Innovation & Disruption

What pain point in the healthcare system was PicassoMD originally built to solve, and how did that shape your product innovation?

How did you identify the whitespace in the crowded telehealth and virtual care market?

What were the biggest marketplace assumptions you had to challenge—or break—to innovate effectively?

In healthcare, innovation often runs into bureaucracy. How did you overcome friction in scaling PicassoMD’s model?

How do you know when your innovation is truly disruptive vs. just incrementally better?

Market Positioning

What was your original brand positioning for PicassoMD, and how did it evolve over time?

How did you position PicassoMD differently for physicians vs. health systems vs. investors?

What messaging helped you earn trust in a market that is often skeptical of new tech and platforms?

What were the key brand pillars you leaned into to stand out in a noisy digital health space?

How do you define success in positioning—not just in terms of market share, but customer and partner perception?