What to Expect When Quitting Your Job and Starting a Business

(Episode 1 of 2 with Ken Moskowitz)

What to Expect When Quitting Your Job and Starting a Business

Considering quitting your job to start a business is a scary thing. It often comes with a fear of the unknown and a fear of failure. In today’s episode, we’re going to walk through how Ken Moskowitz quit his job to start his business and what he experienced when he did that. We’ll also discuss a strategy Ken used to grow and scale his business and one of Ken’s passions.

Ken “Spanky” Moskowitz is a storytelling expert. He is the bestselling author of the book Jab Till It Hurts. He’s a keynote speaker, and he hosts a podcast called Entre Grow, a brand under which he also does some consulting. He’s also the founder and CEO of Ad Zombies. 

Ken’s Journey to Entrepreneurship

Ken’s entrepreneurial journey started when he was just 10 years old. In the 1970s, there was a gas shortage that caused huge lines at the gas stations. Ken saw this as an opportunity to make some money. He went up and down the lines, asking people if they needed coffee, donuts, or newspapers while they waited. He earned thousands in tips for this first entrepreneurial venture.

When he was older, Ken went into the broadcast industry. He spent many years as a creative director and loved what he did, but he always had a side hustle (an outside production company, a mobile DJ company, and built a high-end wedding photography business). 

Over time, Ken started to develop a sour taste for the way he was being treated. “I felt like I was the one who was landing all the big accounts and big clients for the company, and yet, I was never rewarded like the salespeople were because I was the creative guy. So I got a pat on the back and a pizza, and they got to go on the Mexican Riviera cruises with the clients. It didn’t feel right to me,” Ken said.

In December  2010, Ken was at dinner with his boss and he said, “I don’t know what else I could do here; I feel like I’m done.” This was the start of his journey to working for himself. A few months later, he had figured out what he was going to do, and he left the company that everyone thought he would stay at until he retired.

“I went out on my own, and it was the best decision ever. Scary, but the best decision ever,” he said. “Sometimes the biggest rewards come from the scariest steps.”

What to Expect When Choosing to Pursue Entrepreneurship

Choosing entrepreneurship, though our heart may be telling us it’s the right decision, can feel like stepping out of the light and into the darkness. We don’t know what’s out there, and we can’t see what the next step will be.

Here are a few things Ken experienced when he made that decision that many starting entrepreneurs have also experienced.

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A Burning Desire

Often the thing that propels entrepreneurs to take that step is a burning desire. It may be a desire for something more, a higher purpose in our life. It may be a desire for the freedom that entrepreneurship gives us.

Once we realize we have this desire, it is hard to ignore. Ken felt his heart saying, “You’ve got to do this. You’ve got to do this.”

Outside Help

One thing that helped Ken take that first step was his connections. He had many people cheering him on and saying, “Whatever you do when you go out on your own, we would love to continue to work with you. We would love to be clients.”

Several of his first clients came from the clients of the company he was leaving. “If it wasn’t for those relationships that I had developed over my many decades in the broadcast industry, I don’t know that my business would have gotten off to the successful start that it did.”

We can’t start a business on our own. Whether it’s the support of a spouse or the business from past clients, we have people who are willing to help us succeed. Don’t be afraid to reach out to these people and ask for their help.


Ken was very drawn to the freedom that entrepreneurship offers. Part of his burning desire was to be able to control more about his work.

He remembered loving the newfound freedom with his clients. He loved being able to drive his work for them the way he wished he could have when he was working at his corporate job and didn’t have that flexibility or luxury.

Entrepreneurship allows us to control many aspects of our business. This can be liberating and give us great satisfaction with our work. 

Have a Plan B But Don’t Give Up Easily

Ken knew that in a worst-case scenario he would be able to go back to the broadcast industry because they were devastated when he left. At the same time, he didn’t let this plan B hinder him from fully trying.

He thought to himself, “It’s go time,” and he hit the ground running. Failure wasn’t an option for him; though there were some tumultuous times, in the beginning, he didn’t let himself fall back on his plan B too early. He let himself figure it out, and he got through it. 

As with any new thing in life, it can be a good idea to have a backup plan. We just shouldn’t let this backup plan become our crutch or excuse for not really trying.


The first few months after his step into entrepreneurship, Ken felt lonely. In the corporate world, there were daily check-ins and plenty of human contacts. “Suddenly, I was on an island by myself, and it was very lonely. I remember, at times, feeling despondent and a lot of sadness because I missed those relationships,” he said.

At first, entrepreneurship can be lonely. As our business grows, however, we will be able to interact with more clients and employees and have that human connection in our lives.

Wearing Many Hats

At first, Ken didn’t have the money to hire people to help him with the other areas of business. He had to wear the sales hat, the bookkeeping hat, the IT hat, etc. when the only hat that had fit him before was the creative one. 

Ken managed it though, and eventually, he was able to hire people that wore all those hats better than him. It may be hard for us to pick up these hats and put them on as we start our business, but doing so will give us the freedom we long for in our career, and we too will eventually be able to pass on the hats to those who wear them better. 


This may seem contradictory, but being an entrepreneur is often more secure than having a corporate job. As an entrepreneur, we are in control. We won’t be let go when a business hits hard times.

When the pandemic hit, thousands of people were fired, but all those who were entrepreneurs didn’t fire themselves. They figured out how to pivot and adjust their businesses to do things better and more efficiently. Sometimes this security comes with more work because we have to hustle to figure out how to pivot, but we’ll only lose our job if we let it happen to ourselves.

How to Grow and Scale a Business through Partnership or Employees

In 2017, Ken accidentally started a new business called Ad Zombies. He was in a Facebook group and helped someone rewrite a poorly written ad. That was how it started; he helped someone in need without expecting anything in return. 

Ken found that the more he gave, the more the business grew. A few months later, the business was taking off, but Ken didn’t have any systems or processes in place. He brought in writers to help write ads, but he didn’t really have any organization.

Earlier in his career, Ken had met Gary Vaynerchuk at an event and he had casually stayed in touch with him over the years. When Ad Zombies started growing rapidly, Ken sent Gary an email, saying, “Hey, on my next trip to New York I’d love to get together with you for dinner. I started this business by accident and it’s taking off. I’m trying to figure out what to do with it. I have no idea what I’m doing.”

Gary invited Ken to an event he was hosting. Ken flew to New York to join Gary at the event. Ken explained what had happened with the business, how it had grown, and where they were at financially.

Gary told Ken, “You have at least five people in your social circle that have built and scaled an eight- or nine-figure company. Why don’t you reach out to them and give them a piece of the business, give them an equity play in your company? They’ll see what you’ve built so far, and you can give them the opportunity to help you grow and scale because that’s their superpower.”

Ken thought it was a great idea, but the only problem was that he didn’t know who these people were in his network. He couldn’t think of anyone who could help him do this. After a couple of days, Ken was able to come up with some names. He met with the first name on his list, Brandon Disney, and they quickly became business partners.

Ken said he would absolutely recommend this strategy. If we are looking to grow our business and keep it, we can give up 20% equity to a partner who can help us grow and scale. If we want to grow and sell, we should hire someone to help us grow the business so we don’t have to give up equity for the eventual sale.

Ken’s Passion: Foster Care and Adoption

Ken and I share a passion for adoption and helping children find their forever homes. Ken and his wife have fostered 19 kids and have adopted three. 

Ken said, “I think there aren’t enough people who are willing to open up their homes to children right in their own communities that need loving families. So, we are hugely passionate about it. We support foster and adoption agencies in our home state and encourage you to look into it if you’ve been thinking about having kids, but don’t want to have your own and have the heart and the space for a kid that needs a forever home.”

Key Takeaways

Thank you so much Ken for sharing your stories and insights with us today. Here are some of my key takeaways from this episode:

  1. Sometimes the biggest rewards come from the scariest steps.
  2. We have people who are willing to help us succeed and shouldn’t be afraid to reach out to these people and ask for their help.
  3. Entrepreneurship allows us to control our lives and our work.
  4. We may want a plan B when starting a business, as long as we don’t let this stop us from truly trying.
  5. At first, entrepreneurship can be lonely. As our business grows, however, we will be able to interact with more clients and employees and have human connections in our lives.
  6. Entrepreneurship can provide more security than a corporate job.
  7. If we wish to grow and scale our business, consider bringing on a partner or hiring someone with the skills to help us do that.

Connect with Ken

To learn more about or connect with Ken:

Next Steps

  1. Get my free ebook about passion marketing, and learn to identify and leverage the highest passions of our ideal customers at PassionMarketing.com.
  2. Subscribe to Monetization Nation on YouTube, Instagram, Twitter, our Facebook Group, and on your favorite podcast platform.
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    About the author

    Nathan Gwilliam

    Nathan Gwilliam

    I help organizations navigate tectonic shifts that are transforming the business landscape, so they can optimize marketing, accelerate profits, and make a greater difference for good.

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