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?

He’s led recruiting across Asia for some of the world’s most iconic companies—Google, Uber, and Netflix. Now, he's turning his focus to the future of work as the founder of TalentStories, a talent content, consulting and community platform for the curious, the bold, and the optimistic on their journey to find meaning and purpose in a new and changed world of work.

I’m Jason Siegel, founder of Bluetext, and in this episode of Digital Doorways, Aki Taha and I explore the disintegration of traditional work structures, the rise of decentralized teams, and how leaders can adapt to stay human in an increasingly digital world. We talk about the power of storytelling in shaping culture, the skills and mindsets needed to thrive in this new era, and what it really takes to build connection and purpose in the workplace today. If you're curious about where work is headed, this conversation is one you don’t want to miss.

Welcome back to Digital Doorways, where we dive into the branding, positioning, and strategic shifts shaping the business world. Today, we’re tackling a critical transformation in the public sector market—one that every government contractor needs to be paying attention to: the rise of DOGE—the Department of Government Efficiency—and what it means for the future of federal contracting.

Joining us is Cheryl Waldrup, a branding, positioning, and marketing leader with deep expertise in public sector markets. She’s worked with top government contractors to refine their messaging, reposition their brands, and navigate shifting federal priorities. With DOGE rewriting the rules on contracting efficiency, vendor selection, and innovation mandates, the question is: How do firms adapt, stand out, and win in this new environment?

Today, we’ll explore how government contractors must rethink their branding, how they can reposition for success, and what best-in-class marketing strategies look like in this evolving landscape. Let’s get into it.

Welcome to another episode of Digital Doorways Presents: The DealMakers, where we bring you exclusive insights from the top minds in M&A, private equity, and government contracting. Today, we’re diving deep withGreg Van Beuren, Managing Director at https://hl.com/https://hl.com/, the #1 M&A advisory firm in the world in 2024, leading a staggering 415 global transactions—more than any other firm on the planet. Greg has spent over 25 years advising middle-market companies, closing 100+ major deals in government services and technology, working with industry giants like Booz Allen Hamilton, Guidehouse, and The Carlyle Group. If you’re in the dealmaking space, you won’t want to miss this conversation.

Today, we’ll explore what truly drives value in M&A beyond the balance sheet—how messaging, brand positioning, and go-to-market strategy can make or break a deal. Greg will break down why branding isn’t just about perception—it directly impacts deal value and how companies that position themselves as thought leaders gain a competitive edge in the M&A process. We’ll also discuss how refining a go-to-market strategy can transform buyer confidence and turn a struggling deal into a high-value acquisition. Whether you're an executive looking to position your company for sale, an investor assessing market opportunities, or just fascinated by the art of dealmaking, this episode is packed with real-world insights you can’t afford to miss. Let’s get into it.

Welcome to Digital Doorways Presents: The DealMakers. I’m your host, Jason Siegel, founder of Bluetext, and today we’re diving into the art and strategy of M&A with one of the industry’s leading voices—John Song, Managing Director at Baird. John has spent decades advising companies in the government and defense sectors, helping them navigate complex transactions while strategically positioning their brands for maximum value. His expertise goes beyond the financials—he understands how messaging, positioning, and branding can fundamentally impact a company’s valuation and its appeal to potential buyers.

Since 2021, the Baird Defense & Government team has executed 60 transactions, totaling $30 billion in transaction value, solidifying their position as one of the most active investment banking groups in the sector. In this conversation, we’ll explore how a well-crafted narrative can shape deal success, why go-to-market strategy matters in M&A, and how thought leadership can be a game-changer in competitive markets. Whether you're an entrepreneur, an investor, or a dealmaker, this episode will provide invaluable insights on how to build, position, and sell a business for maximum impact. Let’s get started.

Welcome to Digital Doorways Presents: The DealMakers, the podcast that explores the strategies, insights, and behind-the-scenes stories of the world’s top dealmakers. Hosted by Jason Siegel, founder of Bluetext, this series dives into how transformational deals are made, from vision to execution.

In the debut episode, Jason is joined by Kevin DeSanto, co-founder and managing director at KippsDeSanto, to explore:

• What it takes to identify and execute high-stakes deals.
• How industry trends and technology are reshaping the dealmaking landscape.
• What lessons Kevin has learned from leading some of the most impactful transactions.

Get ready for a deep dive into the art and science of dealmaking, featuring insights that will inspire and inform anyone in business. Follow now to unlock the stories behind the deals that shape industries.