Seven lessons from a 10 year entrepreneurial journey

entrepreneurial journey

This is the tenth anniversary of having my own entrepreneurial journey. The only reason I know this is because I received about a million “congratulations on your work anniversary” messages on LinkedIn. I really need to change that setting.

Nevertheless, I’m proud of making it as an entrepreneur this long, and most happy about the amazing connections I’ve made around the world … like you!

This might sound weird, but I’m not creating a special logo, I’m not having a worldwide celebration, I’m not doing anything different at all. Maybe I’ll have a nice dinner with my wife. Point is, I realize the only person who really cares about this work anniversary is me, so I won’t burden you with logo revelry.

However, I’ve reflected on this entrepreneurial journey and I’m challenging myself to do something out of my box today. I want to talk a little about what I did right in my 10 years as an entrepreneur. I normally dwell on mistakes and improvements I need to make, but today I’ll write about what worked, and maybe it will help you on your own career.

1. Experimentation before commitment

I had a great career in the corporate world but started experimenting with outside marketing consulting on the side. I grew comfortable that I would have a ready market if I left the corporate world and that I would enjoy the work.

During the early days of my business, I experimented often with big and small ideas but never got myself into a hole so big that I couldn’t get out of it.

By the way, this was a difficult discipline. When I started my business, the internet and social media were still the Wild West. There were new ideas and new opportunities at every turn. So it took discipline to make the right decisions and open the right doors, instead of rushing through every door!

2. The benefit of a cushion

When I advise people looking to move from a steady job to an entrepreneurial journey, I ask them if they are prepared to be broke for two years. If you are desperate for cash flow, you cannot make smart decisions to grow the business in a patient way. At the first little bump in the road, your whole plan can fall apart.

I learned this the hard way when I invested in a start-up and I KNEW the founder was going to have cash-flow issues (and a baby on the way). I followed my heart instead of my head and that was just dumb. Sure enough, he ran out of cash and started making desperate decisions.

Don’t be so in love with your idea that you’re blind to financial realities.

3. No monetization strategy

This might sound like a failure, but it was a mindful decision. As my “second career” was beginning, I was being pulled in all directions. I didn’t specifically know where most of my money would be coming from.

Would it be books?





It was all new to me as I was making my way in this entrepreneurial world. So I made a crazy decision. I decided to just wait. I was going to let the world tell me what it wanted. This is one of the benefits of that financial cushion I talked about. Instead of desperately trying to find customers, I let the customers find me.

For a strategy-driven guy, this was hard to do, but it was the right decision. Today my strategy is more refined, but I benefitted from patience.

4. Quick pivots

The early days of a new business are crazy. Just adding one customer can add a whole new complexion to the business.

One of my early revenue sources was web development strategy. I was sort of the interface between business owners who needed to build a business on the web and the developers. I had guessed correctly — this was a successful niche — but I learned that I hated the work. I was being dragged down into daily details and I am definitely a big-picture kind of person.

Finally, I had a client (a well-known author) take advantage of me and stiff me for about $4,000. That was the last straw. I needed to paint on a bigger canvas and end this part of my business.

The PR legend and pioneer Harold Burson once told me that his business success came from a keen sense of knowing which doors to open, and which doors to close.

I would add to that. As an entrepreneur, you have to know which doors to open and which to close quickly!

5. Take time to learn to be a business

Before I started my own company, I had 25 years of business experience and two master’s degrees. But I still had a LOT to learn about the routine and flow of being a business owner and the ups and downs of the entrepreneurial journey.

Be humble. Start small things that can lead to big things. Listen to people wiser than you, especially your customers. Give yourself time to adjust to being an entrepreneur.

6. I stopped looking at the balance sheet

This will seem like the craziest idea of all, and I realize it will not be for everybody.

I was really fortunate in that in the first eight years of my entrepreneurial journey, I had continuous year-on-year growth. I had matched my former corporate salary in about 30 months.

It was fun to see that profit line going up every month, but I realized that at this point in my life — my 50s — I was measuring the wrong things. I wanted to work a little less, have more fun, and choose projects I would really enjoy. Watching the money every month was driving the wrong behaviors.

So starting in 2016, I didn’t look at Quickbooks one single time. I just sort of went with the flow. And, I did end up having record years in 2016 and 2017. This year? I don’t know. My business manager takes care of all of that — I haven’t looked at it!

7. Content and the entrepreneurial journey

When I started my business, I experimented with blogging and published some posts when it seemed convenient. After about nine months, I realized that nearly all my new business benefits were coming through the blog and that I needed to get serious about it.

From that point on, I created content on a consistent basis. This was a time before “content marketing” was a thing. For me, blogging was establishing a presence on the web that made a difference.

My advice is to pick one channel and stick to it. I didn’t diversify into podcasting for five years. I could not do anything that would jeopardize the quality of the blog or cheat my blog audience. I see too many people trying to do everything and be everywhere and that is impossible. You can’t be everywhere and be great.

Today a business is built on the awareness that leads to trust, that leads to loyalty, and then, maybe, a purchase. There is no more effective way to start that process than through effective content creation, and there is really no shortcut to that formula. The benefits may not accrue for several years … but becoming known is really the only sustainable competitive advantage you have today and that has to come through some sort of content.

I have not spent one dime on advertising my business … the business grew through content and the authority that comes from that content.

And, thanks.

Whether you subscribe to my blog or podcast, enjoy my marketing books, or you have hired me to speak or help you with your marketing strategy, thank you for your support of my entrepreneurial journey.

I am a bit of an introvert but enjoy telling stories to friends, which is what you have allowed me to do for 10 years. Thank you so very much. I will never take you for granted.

Love, Mark

Keynote speaker Mark SchaeferMark Schaefer is the chief blogger for this site, executive director of Schaefer Marketing Solutions, and the author of several best-selling digital marketing books. He is an acclaimed keynote speaker, college educator, and business consultant.  The Marketing Companion podcast is among the top business podcasts in the world.  Contact Mark to have him speak to your company event or conference soon.

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