Jason Sherman

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Jason Sherman Jason Sherman is a successful entrepreneur, award winning filmmaker, published author, tech startup expert, and journalist.

Most books on how to succeed have been written by millionaires who were in the right place at the right time. Those books simply don’t work for the masses. Everything in this guide is easily replicable and anyone can do it. All you need is determination, patience, and the acceptance of the mistakes you will make.

10/14/2026

The physical war might have just started, but the cyber conflict has been raging for years. Think back to the 'Sandworm' attack that shut down Ukraine's power grids twice. It all began with readily available tools, a chilling warning shot across the bow.

10/13/2026

You can have thousands of leads, but if your churn is high or paid user conversion is low, scaling becomes impossible. What's preventing businesses from reaching that next level of growth?

10/12/2026

Stop brainstorming conversations from being dominated by one voice. Instead, have everyone capture their responses *before* discussion. Then, play them back. This technique ensures 100% of original ideas are heard, fostering true collaboration and maximizing optionality for your team.

In this episode of Strap On Your Boots, I explain why adding more features isn't always the answer when your startup str...
10/12/2026

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.

Listen to the Podcast: https://bit.ly/3UhINax

10/10/2026

The fear of starting over can hold us back from pursuing new paths. But what if the worst-case scenario is simply a chance to rebuild and redefine your journey? Don't be afraid to shift your career, change your mind, or alter your path. True fulfillment lies in embracing change.

10/09/2026

Filmmakers are finding incredible funding opportunities. Imagine depositing $1M and getting a $5M loan for your next project. It took years to build these connections, but the doors are opening.

10/08/2026

Their code quality assurance is larger than any other entity. They've built a sophisticated ecosystem, mastering outsourcing and marketing by utilizing our own tools. Their training playbook is truly insane.

10/07/2026

Companies often hit a wall when their economics improve but they can't scale without significant VC funding. It's a vicious cycle: you need investment to pump into ads to reach revenue goals, but you can't get the investment without hitting those goals first. Understanding how to break this pattern is key.

10/06/2026

Imagine something goes wrong at work and your team needs to talk to you about it. This approach gives everyone the keys to call out issues respectfully, fostering a shared language and trust. It's about getting things on the table early, assuming good intent, and asking how best to approach sensitive conversations. This method builds a stronger, more accountable team.

10/05/2026

Don't assume a big name guarantees success or that cheap means affordable. The most expensive work is often the cheapest. Finding the right vendor means looking beyond these motivators to find that perfect balance.

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Philadelphia, PA

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+12153968577

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