May 11, 2021

The Virtual CMO Podcast, User Engagement
The Virtual CMO Podcast

The Virtual CMO Podcast

Season 5, Episode 1

Hosted By: Eric Dickmann
With Guest: Jason Sherman

Our Featured Guest

Jason Sherman

Author- Strap On Your Boots

Host- Strap on YouR Boots Podcast

Jason Sherman is an entrepreneur, award-winning filmmaker, startup expert, podcast host, and author of Strap On Your Boots.  

Sherman has been featured by several media outlets including the Wall Street Journal, USA Today, The Verge, and ABC News. Jason is fluent in Spanish, is a classically trained violinist, and was a featured speaker on FOX’s Futurist TV Show: Xploration Earth 2050. He runs a web and mobile dev shop and film studio from Philadelphia, Pennsylvania.  gives guest lectures at area universities, and regularly supports hackathons or tech events as a mentor and judge. His methodologies on entrepreneurship and data-driven decisions are his main source of education to those he helps all around the world.

What's Hot?

"If you are an entrepreneur who has hit a wall and aren’t sure how to break through it, then this guide is written just for you. Or if you are just starting out in the world of startups, then save yourself thousands of dollars and a couple years of your valuable time by reading this book before you start your company."

Strap on your Boots  by Jason Sherman is the culmination of Jason's life’s work to help other entrepreneurs succeed and is the focus of a class he created called Startup Essentials.

Jason originally taught the course as a guest lecturer at area universities, including the Wharton School of Business and now the course is available online for students on Udemy.

Grab your copy on Amazon

Strap On Your Boots by Jason Sherman

Jason Sherman

You have to look at the market and how it changes. What might be hot six months ago might be completely dead today. So just dumping more money into the same campaigns doesn't make any sense, you know? I've seen it happen a million times."

What We Discussed with Jason

On this episode, host Eric Dickmann interviews Jason Sherman about understanding your target audience and driving user engagement. Jason is a successful entrepreneur, award-winning filmmaker, published author, tech startup expert, and journalist. Here are some highlights of our conversation:

  • [00:03:41] Everybody can be a content creator! - Jason Sherman shares that he is blown away by the film industry's paradigm shift from bulky DSLRs and expensive film equipment to mobile phones. You can create a simple script, shoot in nearly any location you want, and create content. In fact, his latest documentary was just shot on his iPhone!
  • [00:06:14] A common mistake of entrepreneurs - The number one mistake Sherman sees in many entrepreneurs is that they think their target market is everybody. Instead of focusing on a specific niche where they can be successful, their fear of giving up any business pushes their focus too broadly which slows growth and increases marketing expense.
  • [00:09:05] Businesses do not do much A/B testing  - Jason explains that many entrepreneurs invest too much of their advertising budget on one campaign without doing any testing and experimentation. It is better to try small experiments to see what messages resonate best with your target audience than to plow ahead with a large scale campaign that hasn't been tested.
  • [00:12:26] In any business, iteration is key!- You can't skip a step or take a shortcut just to save money and time. It's important to follow a process to be successful in your business. The steps are there for a reason. Follow the steps and iterate as needed to find something that works.
  • [00:13:28] What can businesses do with a small marketing budget ? -Jason shares the three ways to impact the market even with a small budget: engage your customer, be a subject matter expert in your industry, and create a simple website to bolster your brand. 
  • [00:22:00] How can I stand out in the market? - There are many businesses that offer similar products or services to what you are selling. If you are an entrepreneur who truly wants to stand out and be revolutionary, Sherman urges you to find the ultimate pain point faced by customers, dig deep and come up with a unique way to be the first one to solve that specific problem. 
  • [00:29:09] What works online? - Jason shares that it's tough to predict what will happen in the future. The market has seen a move from a lot from  paid ads to the rise of influencers creating their own content and publishing it on their websites or social media accounts. However, Jason encourages companies to get a mix of both paid ads and organic content for lead generation. Getting a celebrity on board is always going to help but that's not always very practical. 
  • [00:31:25] Stand up and be productive! - The pandemic and tight restrictions have caused many of our schedules to be disrupted and has hurt productivity. Jason encourages you to get up off the sofa, put down the bag of chips, and create something...anything! Creating valuable content can make a meaningful impact on your business for months to come.

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Eric Dickmann

About the author

Eric Dickmann is the Founder / CMO of The Five Echelon Group, host of the weekly podcast "The Virtual CMO" and YouTube series "Work-Life" and a fractional CMO for a variety of small and midsize companies. An executive leader with over 30 years of experience in marketing, product development, and digital transformation, he has worked with large, global companies and small startups to develop and execute marketing strategies to bring innovative products to the market.