Strap on your Boots

Hosted by Jason Sherman

Business EducationInterviews guestsExplicit

Website RSS feed

Episodes

379

Latest episode

Oct 2026

Language

EN-US

About the show

Successful technologist and filmmaker Jason Sherman gives you real world examples on how to realistically succeed in the world of entrepreneurship while helping you avoid common mistakes. His methods and strategies apply to any industry, income or education level. You will also learn from industry experts, entrepreneurs, CEOs, and business owners as they talk about their successes in his segment Zero to CEO. Lastly, you can hear about future technologies and space phenomena in Jason's favorite segment: Future Tech. So get ready to Strap on your Boots! ]]>

Listen to episodes

60 recent

October 26, 2026Episode 37816 min

Episode 378: Is It Becoming Too Easy to Start a Company?

In this episode of Strap On Your Boots , I explore how artificial intelligence is transforming entrepreneurship by making it easier than ever to turn an idea into a working product. Drawing from my early experiences building Gugo, Picklify, and Instamour, I reflect on the years when launching a technology startup required expensive developers, complicated programming, and months of work. Today, tools like Cursor, Claude, and ChatGPT can help entrepreneurs build functional applications in days. But while the technology has changed dramatically, the biggest challenge remains the same: finding customers who actually want to use what you've built. I explain why building a community, getting your first 100 users, collecting feedback, and learning how to market your product are more important than ever.

October 19, 2026Episode 37714 min

Episode 377: How to Find Customers for Your Startup

In this episode of Strap On Your Boots, I explore why marketing a technology startup can be so much harder than promoting a movie. Drawing from my experiences building Instamour , Spinnr , Vengo AI , and Campus Pixel , I explain how changing products, shifting customer markets, and evolving business models can make startup marketing a constant challenge. I also share how I marketed my documentary Before the Moon , combining grassroots community outreach, social media, local publicity, and targeted advertising to sell out an 850-person premiere. Whether you're launching software or promoting a creative project, understanding your audience before spending money on marketing can make all the difference.

October 12, 2026Episode 37615 min

Episode 376: Why More Features Won’t Save Your Startup

In this episode of Strap On Your Boots , I explain why adding more features isn’t always the answer when your startup struggles to attract customers. Drawing from my years running a technology consulting company, I share how founders often spend months building complicated platforms before discovering whether anyone actually wants them. We explore why launching a minimum viable product (MVP), listening to customer feedback, and focusing on the core value of your product can save time, money, and frustration. Sometimes the smartest move isn’t building something new. It’s figuring out why people aren’t using what you’ve already built.

October 5, 2026Episode 37516 min

Episode 375: Why Entrepreneurs Should Stop Watching Their Competition

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.

September 28, 2026Episode 37417 min

Episode 374: How to Access $1 Million or More in Business Funding with Michael Praver

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.

September 21, 2026Episode 37317 min

Episode 373: Why Bootstrapping a Startup Is Becoming Cool Again

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.

September 14, 2026Episode 37217 min

Episode 372: Investing in the AI-Driven ROAS Economy with James King

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.

September 7, 2026Episode 37118 min

Episode 371: Why Independent Filmmaking Is Easier Than Ever

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.

August 31, 2026Episode 37019 min

Episode 370: Why Investors Want Revenue, Not Just a Great Idea

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.

August 24, 2026Episode 36916 min

Episode 369: Why Five-Year Business Plans Don't Work Anymore

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.

Is this your show?

Claim this listing to keep it up to date, reach guests who want to pitch you, and manage bookings with Guestify.

Claim this listing

More Business podcasts

Business Of Weather | Weather Intelligence For Improved Decision Making

BusinessTechnology

Domain Details Page

BusinessInvesting

The Bottom Line

Alexander Spencer

BusinessInterviews guests