Strap on your Boots

In this episode of Strap On Your Boots, I explore why studying your competition can be valuable, but watching them too closely can actually hurt your startup. Drawing from my experience building products like Spinnr, I discuss how competitor research can lead to feature creep, distract from your original vision, and create unfair comparisons with companies that have far more resources. Instead of constantly reacting to what competitors are building, I’ve learned to focus more on customer behavior, repeated feedback, and the specific problem I’m trying to solve.

In this episode of Zero to CEO, I speak with Michael Praver of FundingFundingFunding.com about the process of raising capital for a startup or business expansion. Michael walks through the funding process from beginning to end, including business credit, bridge funding, shelf corporations, corporate funding, and how entrepreneurs can position themselves to access larger amounts of capital. We also discuss what founders should understand before taking on funding, how different financing strategies work, and what businesses should consider before putting that capital to work.

In this episode of Strap On Your Boots, I explore why I’ve become increasingly interested in building companies with customers before turning to investors. Drawing from my experience with Instamour, Vengo AI, Campus Pixel, Spinnr, Axopods, Ortempo, and even my documentary Before the Moon, I look at how much cheaper and faster it has become to launch something today. Bootstrapping isn’t about avoiding investors at all costs. It’s about building the product, finding customers, generating revenue, and removing as much risk as possible before deciding whether outside capital can actually accelerate the business.

In this episode of Zero to CEO, I speak with James King, founder and fund manager at ROAS Fund, about an emerging investment opportunity created by the way businesses acquire customers through platforms like Meta and Google. James explains what he calls the “ROAS economy,” how AI-driven advertising has created new inefficiencies in the market, and why measurable business revenue could become an alternative investable asset. We also discuss private credit, diversification, risk, and the lessons James has learned from more than a decade of building and investing in digital businesses.

 In this episode of Strap On Your Boots, I reflect on nearly twenty years of independent filmmaking and why I believe there has never been a better time to make a movie. Using my latest documentary, Before the Moon, as an example, I explore how affordable cinema cameras, drones, editing tools, social media, direct screenings, physical media, and digital distribution have transformed what independent filmmakers can accomplish. The technology is more accessible than ever, but the real advantage comes from finding a great story, building an audience around it, and creating something people genuinely want to see. 

 In this episode of Strap On Your Boots, I reflect on how startup fundraising has changed since I first entered the tech world and why I’ve become far more focused on revenue than raising capital. From growing Instamour to roughly half a million users without solving monetization early enough, to building companies today around paying customers and enterprise contracts, I explore why proving people will actually pay may be the most important validation a founder can get. Fundraising can accelerate a business, but raising money shouldn’t be confused with actually making money. 

In this episode of Strap On Your Boots, I explore why I've stopped treating five-year business plans as predictions of where a company will actually end up. After years of building startups, I've learned that customers, technology, competition, and entire markets can change faster than any spreadsheet can anticipate. I share how Vengo AI evolved from consumer to B2B SaaS to enterprise, why I now plan more specifically for the near term, and how founders can balance having a long-term direction with staying flexible enough to respond when the market tells them something new.

In this episode of Zero to CEO, I speak with Dr. Bruce Dorey, leadership expert, executive coach, and engineering CEO, about one of the biggest challenges organizations face today: preserving decades of institutional knowledge before it walks out the door. We discuss why experience is far more valuable than documentation alone, how mentorship and coaching help develop future leaders, and how AI can capture and scale human expertise without replacing the people behind it. If you’re leading a business or preparing your organization for the future, this conversation offers practical insights you can apply today.

In this episode of Strap On Your Boots, I explore one of the biggest advantages startups have over much larger competitors: speed. Drawing from my experience building companies and the evolution of Vengo AI from a consumer product to B2B SaaS and eventually enterprise, I explain how small teams can listen to customers, test ideas, pivot, and respond to the market incredibly quickly. Large companies may have more money, people, and resources, but all of that size comes with organizational weight. Sometimes the startup that can adapt in days has an advantage that money simply can’t buy.

In this episode of Strap On Your Boots, I reflect on turning fifty and the biggest lesson I've learned after decades of building startups, making films, writing software, and exploring new ideas. Experience isn't just about accumulating knowledge. It's about developing judgment, recognizing patterns, and connecting lessons from projects that once seemed completely unrelated. I share how curiosity, failure, and continuous learning have shaped every stage of my career, and why your greatest advantage as an entrepreneur may be the experiences you've already lived through.