Jason Sherman

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.

06/19/2026

Traditional ads are losing their impact. Today, customers trust real people more than brands. User-generated content feels authentic, is affordable to create, and converts. It's a game-changer for sellers.

06/18/2026

Scaling your business means knowing yourself and what you offer. Trying to be everything to your first few clients leads to running multiple systems, hindering growth. Define your services and boundaries to truly scale.

06/17/2026

Many of us were told to start our own businesses, but a new trend is emerging: millennials are buying established, six-figure businesses from retiring boomers. They scale them, and then resell or keep them operational for steady profit.

06/16/2026

As a leader, putting your own oxygen mask on first isn't selfish—it's critical. Self-care empowers you to effectively care for others and your business. Sometimes, transitioning from CEO to executive chairman allows you to focus on innovation and strategy, which is where your true energy lies.

06/15/2026

Salespeople often pitch before truly understanding the client's needs. It's like a doctor prescribing surgery without asking questions. Genuine discovery builds trust and ensures your solution is the right fit, aligning both head and heart.

In this episode of Strap On Your Boots, I reflect on how startup culture shaped my view of entrepreneurship and why I re...
06/15/2026

In this episode of Strap On Your Boots, I reflect on how startup culture shaped my view of entrepreneurship and why I recently found myself questioning one of my own assumptions. After learning about entrepreneurs who buy existing businesses instead of building companies from scratch, I began wondering whether we've become too attached to a single version of what entrepreneurship is supposed to look like. I share lessons from my own journey building startups and explore why sustainability, ex*****on, and long-term value creation may deserve just as much attention as innovation and growth.

Podcast: https://bit.ly/4vR9xvH

06/13/2026

The pandemic shifted mindsets, pushing more people to explore direct-to-consumer businesses. But how do you stand out when the market is flooded? User-generated content is key. Think raw, real, and relatable – like a genuine recommendation from a friend, not a polished ad.

06/12/2026

Growing a business can strain your culture and values. I prioritize treating everyone with kindness, respect, and compassion. We give the benefit of the doubt, avoid drama, and focus on fixing problems collaboratively, not with animosity.

06/11/2026

Putting your own oxygen mask on first isn't selfish, it's critical. Leaders must prioritize self-care like resetting, renewing, resting, and reflecting to effectively care for others.

06/10/2026

Our parents' generation was taught real estate and stocks. But those markets are tough now. Investing in yourself and your ability to improve something, then sell it, might be the best move you can make.

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Philadelphia, PA

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+12153968577

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