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?