In the Trenches: Entrepreneurial Lessons From The Experts

One of the best ways to grow your business is to learn from and be inspired by those who live in the same trenches. The people who exude what you want to be, who have fought the struggle, and who continue to excel regardless of how times change. I’m just a few months into my baby startup, so I thought I’d get some pearls of wisdom from folks I look up to. I was lucky enough to get Copyblogger’s Brian Clark, John Jantsch from Duct Tape Marketing and Atlas Web Service founder (and renowned troublemaker) Michael Gray into a short email interview.

Here’s a bit of what I asked them, what I learned and lessons I think we can all benefit from.

Most entrepreneurs are unemployable: Both Brian and John noted that the reason they work for themselves is that they simply can’t work for anyone else. Brian called himself ‘literally unemployable’, saying it was either this or begging on the street. Similarly, John commented he has some control issues (don’t we all?) and spends his life on the hunt to innovate and try new things – something that’s hard to do when working for someone else. Having just started my own company back in January because I was tired of other people’s rules and conditions, I sympathize with the pangs of John and Brian. Entrepreneurs want more.

The bold thrive in a recession: Michael, Brian and John all stressed that SMB owners can’t be afraid in a recession. Downturns open up and create opportunities more than they take them away. Michael particularly noted that during a recession when sales are slow, the only people doing any business are the big guys and the people who have a love for it. The middle tier who’s just in it for the money loses interest. Hopefully you bring some level of passion to your project and can pick up the disenfranchised middle ground. Coming in at zero during a recession leaves you nowhere to go but up in market share. That said, you still have to have a good business model. According to Brian, SMB owners can boldly steal market share simply by not being afraid.

Staying efficient is one of SMB owner’s greatest challenges: Eliminating time wasters is an absolute must for SMB owners. Michael commented that when you work with a big company, there’s no need for you to be efficient. Sometimes you’re even intentionally inefficient so everyone under you is busy. When you go on your own you have to learn to cut down on the maintenance points. Having something that has to be looked at everyday is good when you have staff, it’s not so good when you are the staff. There are a lot of cool and interesting things you can do when running your own business, but not all of them are profitable. You have to learn to figure out what actions have an influence on your bank account and what things are a complete time suck.

Most entrepreneur wish they’d “jumped sooner”: Now is the perfect time to start a business. Regardless of when “now” is. It will never be easier or more feasible and if you keep waiting for the ‘right moment’, you’ll wait forever. Michael Gray considers waiting an extra 2-3 years to go out on his own a mistake, fully admitting that even when he did do it, he didn’t know enough. The thing is, you learn by doing and by getting knocked on the head by your community elders. You’ll never be “ready” to go on your own until you actually do it. That’s when the learning process starts. Michael would kill to have those few extra years back.

You have to focus on the brand: John Jantsch feels not focusing on his brand was one of the biggest mistakes he made as an entrepreneur. For many years he was content to let the business be about him and what he wanted to do. Today, he’s changed his thinking on that and it’s an excellent point. You need to think beyond just today. What do you want from your business? Most people don’t want to be running the day-to-day. They want to get to the point where they can let someone do the nitty gritty stuff so they can focus on managing. If that’s the case, you can’t brand it around simply yourself. And you need to take steps to put that system in place from the very beginning.

Entrepreneurs value the freedom: Brian commented that freedom was the biggest reward of having your own business (though the money’s not bad either), and both John and Michael agreed. Entrepreneurs love being able to choose when and how they work, even if they do work harder and longer than most people. When you answer to yourself, the clock and calendar become irrelevant. Not being tied to a time clock is a huge bonus for most people.

Social media has made things easier for SMB owners.sort of: Brian called social media tools incredibly powerful for SMB owners because you can reach people without spending money. He joked that he doesn’t understand people who can’t figure out the ROI of social media marketing. Social media is about people. People buy stuff. That’s it.

Michael spoke from the other side, saying that if you’re a small business owner and not tech savvy, it’s changed things for the worse. Communication, networking and business deals are being done and you’re not part of it. The downside is it’s easy to get distracted by all this and not all of it is an efficient use of time and resources. Having 10,000 followers on Twitter is great, but if they don’t visit your Web site, tweet your links, bookmark your pages, or buy from you what’s the point? Social media is a tool just like a hammer, if you know what you’re doing you can build a house, if you don’t you end up with a broken thumb.

Now tell me you don’t want to print this out and sleep with it under your pillow tonight. Careful of the paper cuts.


Lisa Barone Lisa Barone is Vice President of Strategy at Overit, an Albany Web design and development firm where she serves on the senior staff overseeing the company’s marketing consulting, social media, and content divisions.

21 Reactions
  1. How do you manage your time and become your own employer, if you are not employable?

    I managed my time well and worked like a horse in the office, but I can’t manage myself working from home.

    Any tips about this?


    P.S. @RuudHein recommended the 10min work/2min break hourly schedule: anyone tried it?

  2. So in summary; be efficient, don’t waste time, and the right time is now.

    Pretty vague advice. Thx.

  3. The courage to “jump” in a recessionary economy is what truly separates the passionate from the crowd. When you make the jump, make sure to have a network of like-minded people who will give you advice and correction (honestly, which is sometimes harsh), just like Lisa has done.

  4. Great Article. I can’t get enough of Social Media. It is changing the way business is done. Corporate America probably bans the use of facebook and twitter during business hours. This gets back to your point as to why entrepreneurs are unemployable. Too many rules and regs.

  5. You can’t get anything better than thoughts and advice from business owners who have actually experienced it. Good stuff. I love the freedom that working from home has brought me. Being able to schedule appts, not work related like doctors or hair cuts, during day time hours is a great perk. I don’t miss waiting in a doctors office for hours on end at all.

  6. I find the first point the most interesting “most entrepreneurs are unemployable” and it’s kinda funny for me to see that written here because I, myself, have made this observation over the years.

    It’s like taming a wild horse that wishes to run free. And when you do, you take away its passion. If you take an entrepreneurial thinker and someone who likes to work at their own pace and you place them into a cubicle on a rigid time schedule, unfortunately, you might not get the results you were expecting. It’s not that they’re not capable, it’s just that they’re stiffled.

    It’s been an observation that has interested me and caught my attention many times over the years and still intriques me to this day. Thanks for discussing it here – and thanks to John and Brian for their honesty about it.

  7. Thanks Lisa!

    Lotsa “Bingo’s” resonate with me here. Interestingly, a theory of mass psychology suggests attitude of the herd drives the market (; entrepreneurs can position themselves for the market ( Hope this helps.

    As to discipline and distractions, one tip is to remove yourself from temptation. Right now, I’m wondering if I should not remove myself from Twitter or use a kitchen timer. Stop after the “ding.” Or put up a wall/designate a room in the home to isolate from TV and kids. Of course, if things get too bad for too long, a job might be better.

  8. Most entrepreneurs are unemployable: (LOL)

    I just can’t help but laugh on that tip. Because this is me, exactly me!

  9. Martin Lindeskog

    Interesting insights from a creative bunch of small business entrepreneurs! 🙂

    Bianca Aquino: Regarding the aspect of being “employable”, I think that you should do some introspection regarding this issue. I am employable and a lone-wolf freelancer with an individual spirit at the same time. At one level I don’t want to work for the “Man” as the describe it in America, but at the same time I could philosophically speaking be able to defend big business and their important role in the economy. All big companies have started out small at some point in time. It all started out with an idea…

    I have enjoyed both to be employed and working for someone else as long as the company has respected my views and really had a true “gut” feeling about the exchange of value for value. I enjoy very much my time now as being an sole trader (sole proprietor) with my own firm and also working together with others in another company. I am also open to “rent” my employer in certain cases than I don’t want to deal with the hassle of paperwork and other stuff. (I could tell you more about this concept if you are interested. It is smart way for small business owners to hire working force without all the hassle and for the freelancer to concentrate on the real job and task.)

    I will contact some of you regarding a new opportunity that has occurred for me at this moment. I want to get in touch with small business owners and others who are interested in a positive exchange and work together on new projects.

  10. “Most entrepreneurs are unemployable”
    I could not agree more. I see a lot of entrepreneurs and this is very true.

  11. Fun read Lisa! I come across so many articles these days but I read this one all the way through. I have to say, you caught my attention with the “Most entrepreneurs are unemployable” bullet point. It is nice to see that I am not alone. I agree with Chris in that it is like taming a wild horse. I also appreciate and agree with your advice that you have to organize yourself better so that you you know how to focus your time on revenue generating activities as well as focus on your brand. Social media is amazing and growing like crazy, however it is indeed a tool that needs to be used effectively.


  12. @Butler Consultants, Exactly! The proof: they have their own business. 😉

  13. RedHotFranchises

    While i personally think most entrepreneurs have to be employable first before they can become self-employed, but of course there are always short-cuts in Business that a visionary leader may take through daily research and discipline. Time is money. Measure Human Output, Attention to Detail, are you doing the things that you want done throughout the day? Start with a Daily Planner with a scheduled list of things to do at a certain time and plan your day the night before.

  14. @Yura

    Hey man if your still looking at these comments, regarding your advice questions ” How to manage yourself now that you work for yourself?”

    I struggled with the same but what really fixed me is developing a routine that balanced my life and business. I had a schedule just like a job I would work for an employer but it wasn’t rigid and it fit my work style. It allowed me to flow into and out of my work seamlessly.

    So try setting up a routine and a indepth plan of what you’ll get done outlining your target goals for the day and week… Hope this helps.

  15. Ana | Traffic Generation

    Interesting points, Lisa, to say the least.

    First of all, unemployable – it almost has to be that way; otherwise, who in their right mind would ever want to work for themselves? LOL

    I love the bit about creating your brand. Seems to be more and more important especially these days as even search engines are starting to pay more and more attention to brand presence.

    Thanks for food for thought.

  16. And you need to take steps to put that system in place from the very beginning.

  17. If that’s the case, you can’t brand it around simply yourself. And you need to take steps to put that system in place from the very beginning.