EFP 53: Riding The Entrepreneurial Roller Coaster

Justin Cooke

June 27, 2013

Starting a business is definitely not for the faint-hearted or weak-kneed…

Sure, there are some clear benefits to being your own boss…but the up-and-down swings can leave you feeling either elated or downright miserable. The funny thing is that they don’t seem to go away – definitely not on the timetable you’d prefer.

The Big Ups and Downs of the Entrepreneurial Roller Coaster

The GOOD news is that there are some things you can do to make the lows a bit more bearable, while maximizing the value you get out of the highs…and that’s exactly what this episode is about. Joe and I will share some of our experiences with the entrepreneurial roller coaster and delve into how we’ve dealt with them through the years.

Check Out This Week’s Episode Here:

Direct Download – Right Click, Save As


“We were at Outback Steakhouse, literally doing the napkin math (to sketch out our new business)” – Justin – Click To Tweet!

“When you’re losing, that’s not the time to double-down and try to win back your losses” – Joe – Click To Tweet!

“When I got to the PI and was hit by that foreign smell I thought, “Wow, I get to LIVE here!” – Joe – Click To Tweet!

Topics Discussed This Week Include:

  • Webmaster Tools – Is it worth it?
  • High: Your Big Idea
  • Low: Newness Wears Off
  • High: The Work Starts
  • Low: Unforseen Setbacks And Pivots
  • High: Profits And Diversification
  • Low: Another Kick In The Nuts
  • High: Fighting Back With Tweaks And Iterations
  • Low: Becoming Your Own Bottleneck
  • High: Replacing Yourself And New Revenue Streams
  • Low: ???


So…what do you think about using Google Webmaster Tools. Is it worth it? How has your entrepreneurial roller coaster been going…more highs or lows? Give us a shout on Twitter or leave us a comment below and we’ll respond publicly!

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  1. Josh says:

    I was listening to this podcast while going for a jog the other day. Right when you said “A black swan will appear right in front of your face” I looked up and saw that I was on “Swan Circle.” Does this mean that I’m going to get hit with a black swan? Should I be worried?

  2. Keith Mander says:

    There’s a Webmaster Tools API, so you can automate the process of adding sites. You could have developer make it so that you just paste in a list of URLs into a text area and click submit and the job is done (which is even better than the wish of uploading a spreadsheet).

  3. Chad Eisenhart says:

    Thanks for putting on the show. I started listening a few weeks ago and have heard about 20 or so of your past episodes.

    Per the Webmaster Tools discussion:

    Just as someone already mentioned you can submit your site map to Google. Which of course is automatically updated as you add more content (assuming you are using certain SEO or sitemap plugins).

    – You are also notified of site errors.

    – You can test your robot.txt file.

    – Choose the www vs non www version of your site.

    – Submit a site map of your images to drive more traffic to you site.

    I like to look what terms I am getting impressions for and where I rank. But I would look for terms that I am appearing in a lot of search for but I am averaging at the bottom of the 1st page or page 2. I figure this is some low hanging fruit to go after.

    And don’t forget about Bing webmaster tools also!

    • Justin Cooke says:

      Thanks, Chad…

      You’re right about all of the updates…the site errors is particularly useful. I think the benefits far outweigh any negatives here, hehe.

  4. Ben Krueger says:

    Incredible episode fellas! This applies so accurately to my current situation it’s scary. I really got a ton of value from this episode, the different trials and tribulations you guys have faced and a bit of a ‘road map’ of what to expect. Keep it coming!

    • Justin Cooke says:

      Awesome, Ben…glad to hear it helped you!

      Which “stage” in the business do you feel you’re at right now? Maybe we can give you some suggestions on how to get out of the dip or maximize your climb! hehe

  5. Tauno says:

    I have added some of my sites, esp. the top performing sites, but not all of them. Same fear factor here, although I tend to think it can’t hurt the sites anyway. I find the stats very useful and checking it at least a few times every week. Esp. I like to check out the crawl and indexed pages stats and also positions and CTR for top rankings. My top site has reached 900K pages indexed according to Webmaster Tools, but 1.1M show up if I do “site: mysite.com” search in Google.

    • Justin Cooke says:

      Hey Tauno,

      I wonder where the additional pages are coming from with the “site:” search…probably tags/categories, eh?

      I think we’re going to go with Webmaster Tools. Hell, Google knows all anyway with Analytics and AdSense on the sites…WMT can’t hurt right?

  6. 100% yes to webmaster tools google knows everything anyway. Plus you get more info in analytics plus webmaster tools lets you upload sitemaps and do diagnostics. Lastly it can notify you of penalties. I saw some old sites get “thin content penalty” the other day. 1 day test sites from last year

    • Justin Cooke says:

      Yeah, that’s what I’m thinking too, Steve. I wish we could just upload a spreadsheet with the sites, but it really doesn’t take very long…can just have an agent knock it out once a week. It’s just one of those things that slipped through the cracks that we never bothered to correct, hehe.

      Anyone have any reasons we should NOT do it?

    • Iain Robson says:

      Steve is bang on. That’s exactly why you should have webmaster tools.

      The biggest thing is the penalties that you be made aware of. This information would be extremely helpful if you were going to sell the site for instance. That is one of the most important reasons why you should do it.

      The real question is, is that information valuable enough to have someone do it? Not sure.

      If you could make it part of the process from the start, that would be better.

      You could do it from now on, instead of doing the backlog.

      Just some thoughts.

      • Justin Cooke says:

        Yeah…agreed with Steve here. I saw an older site get the “thin content penalty” as well. Funny enough…I actually saw a message for one “manual penalty”…it was the first I’d ever seen.

        I think it probably is worth having someone go through and hammer out the old sites as well.

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