From Microsoft to Making Millions
In this episode of The Breakout CEO Podcast, host Jeff Holman sits down with Steven Selikoff, founder of Product 1 and author of The COMPLETE BOOK of Product Design, Development, Manufacturing, and Sales.
Steven’s journey moves from corporate success at Microsoft to global product entrepreneurship—guided by one principle: profitability must come first. His Willingness-To-Pay (WTP) model flips traditional product development on its head, showing CEOs how to design profitable products from day one while mitigating risk and conquering fear.
For founders navigating complex supply chains, import tariffs, or IP protection in product businesses, Steven’s lessons apply across industries—from ecommerce and retail to SaaS and tech-enabled brands.
The moment: Sometimes, breakthrough ideas don’t come from boardrooms or whiteboards—they come from the chaos of everyday life.
For Steven Selikoff, that moment happened one night at home. His wife had just brought home a new Yorkie. Within minutes, the dog had claimed the middle of their bed. Steven joked, “We need pillowcases that say: ‘The dog sleeps here. The wife sleeps here. The husband sleeps here.’”
By sunrise, he had mapped out a plan to make it real. What started as a laugh turned into a product line that would appear in Bed Bath & Beyond, Francesca’s, and Amazon.
That “Pillowcase Moment” didn’t just spark a product. It sparked a new way of thinking about entrepreneurship—one rooted not in ideas, but in profitability from day one.
The turn: Like many innovators, Steven had spent years in corporate life—most recently at Microsoft, where he led global retail strategy. But the corporate ladder has its limits.
When his pillowcase idea took off, he realized the deeper truth behind his success:
Most entrepreneurs chase products. The best ones design businesses that make money.
Steven saw that even creative, driven founders were building fragile companies—depending on trends, tariffs, or luck instead of structured profitability. That insight became the turning point that led to his signature framework: the WTP (Willingness-To-Pay) Product Development Model.
The breakout: The WTP model starts with a deceptively simple question:
“If this product solved your problem, how much would you pay for it?”
That answer becomes the North Star for the entire product journey—from ideation and design to sourcing, packaging, and sales.
Rather than building something and hoping it sells, entrepreneurs reverse-engineer every decision around that price point. Manufacturing targets, material choices, and even marketing budgets align to ensure a sustainable margin.
It’s how Steven helps founders—many of them scaling ecommerce and retail brands—avoid what he calls the “watermelon truck problem”: selling more but losing money faster.
In a world where tariffs, supply chain volatility, and shifting consumer expectations can erode profits overnight, WTP provides something rare—clarity. It’s a disciplined framework that builds margin, resilience, and IP value into the product itself.
The lesson for CEOs: For scaling CEOs, Steven’s lesson is simple but profound:
Profit isn’t what’s left over—it’s what you build in.
Whether you’re launching a new SaaS feature, an ecommerce line, or a tech-enabled physical product, your model must begin where the customer’s value begins.
Use price as your compass. Engineer backwards. Design your business like a system that protects margin, not one that chases revenue.
It’s the same insight that took Steven from a late-night joke to a global product brand—and now powers Product 1, his accelerator helping entrepreneurs create profitable, durable businesses.
Listen to the full episode for Steven's detailed story and insights.
Steven Selikoff’s story blends creativity, discipline, and courage into a roadmap for sustainable entrepreneurship. His WTP model empowers CEOs to stop chasing revenue and start engineering profitability—from idea to market.
For founders navigating growth, innovation, and the legal complexities of product development, this episode is a reminder that profit is the product—and fear fades when you act with clarity.
Listen to the full episode for deeper insights into product innovation, IP strategy, and building businesses that last.
Steven Selikoff is the founder of Product 1, a global accelerator helping entrepreneurs bring profitable products to market. He is the author of The COMPLETE BOOK of Product Design, Development, Manufacturing, and Sales, and a leading educator in global sourcing, product strategy, and profitability modeling.
Website: Product 1
LinkedIn: https://www.linkedin.com/in/stevenselikoff/
Jeff Holman is a CEO advisor, legal strategist, and founder of Intellectual Strategies. With years of experience guiding leaders through complex business and legal challenges, Jeff equips CEOs to scale with confidence by blending legal expertise with strategic foresight. Connect with him on LinkedIn.
Intellectual Strategies provides innovative legal solutions for CEOs and founders through its fractional legal team model. By offering proactive, integrated legal support at predictable costs, the firm helps leaders protect their businesses, manage risk, and focus on growth with confidence.
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The Breakout CEO podcast brings you inside the pivotal moments of scaling leaders. Each week, host Jeff Holman spotlights breakout stories of scaling CEOs—showing how resilience, insight, and strategy create pivotal inflection points and lasting growth.
Listen and subscribe on your favorite podcast platform:
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Want to be a guest—or know a scaling CEO with a breakout story to share? Apply directly at go.intellectualstrategies.com.
[03:33] Building Businesses from Bricks, Not Straw
Steven challenges entrepreneurs to rethink their cost structure. If your margins collapse when tariffs rise, your business wasn’t strong enough to begin with.
[10:55] From Corporate Ladder to Entrepreneurial Freedom
After 14 years at Microsoft, Steven realized true ownership meant building something himself. His transition was risky—but rewarding.
[15:21] The Pillowcase Moment
A playful idea turned into a best-selling product and a million-dollar business. The real lesson: don’t wait for perfect timing. Act on the idea.
[21:00] The Willingness-To-Pay Model
Steven’s WTP model helps CEOs lock in profit from the start by aligning design, cost, and market value—essential for any growth-stage product company.
[27:00] The Four Fears of Innovators
Jeff and Steven unpack how fear stops founders—and how structured action, smart contracts, and strong product strategy can overcome it.
[34:00] Preparing for Success
Growth creates its own risks. Steven advises CEOs to plan financing, cash flow, and supplier terms early, long before expansion pressures hit.
