Author: Josh O'Brien

Things Change. Some New content.

Once again it has been awhile. But I wanted to get some new content out. This year I was elected as a member of the board for WAA. Part of my time on the board will include writing articles for our membership. From the second I heard this I knew what I wanted to do. I wanted to combine a career in tech with the auction business. For those who don’t know about the side hustles I have going on that will be a post for another day. So with here you go, this is a repost of my first new letter article, Revolutionizing Auctions with Automation and AI. I hope you find it interesting.

Revolutionizing Auctions with Automation and AI

My career up to this point has been in technology. With that has come the need to automate large-scale and tedious tasks. In the past, that would have meant buying expensive tools or learning how to program in a language like Python. But things have changed drastically in the past few years. Now we have cost-effective, highly intuitive, and intelligent tools like Zapier and ChatGPT.

As a quick primer, tools like Zapier integrate with other platforms like Google Docs, Office 365, Mailchimp, CRM, and many others. This allows you to automate tasks that in the past would have been manual and tedious. For example, if you track all of your new consignment users in a CRM, you can automate adding any new consignors to a custom MailChimp mailing list. This would cut down at least three steps of exporting the list and uploading it to Mailchimp, enabling you to have an always up-to-date mailing group to notify consignors of upcoming auctions they may wish to add items to. You can go much further and add multiple steps, but this example is phase 1 of automating the data for your business.

Moving forward, we have AI tools like ChatGPT. This opens up a totally different set of opportunities. We should think of AI tools like this as our specialized assistant. In my case, there are few things I am really good at, a lot of things I can do, and billions of things I will never be able to do well enough to do myself. It is the second two areas where we can leverage this virtual expert. So as an example, I can write marketing copy, but I am not great at it. So I go to ChatGPT and ask the following:

“Please write me ad copy for an online auction starting on April 18, 2023, and closing on May 2, 2023. The auction has something for everyone. The lead items for the ad are a 2005 Jeep Grand Cherokee and a 1975 Starfire 1801 Pleasure with an outdrive engine. Other items in the auction include many kitchen and household items, a video poker machine, vintage video games, vintage board games, many Christmas decorations, and many vintage items. Lots of books. A garage of tools and ice fishing equipment. Please ask me questions to produce the best outcome.”

This simple request, in under 15 seconds, provided me with an over-the-top ad copy and a description for our auction that is running right now. So over-the-top, in fact, I had to follow up by asking the tool:

“This looks pretty good, but can we tone it down just a bit and get rid of emojis?”

To which it responded with a much more reasonable copy that we ended up using. But it’s not just that. I have also used ChatGPT to come up with a variable auction % split for a large customer that we are working with. It was not perfect, but through the conversation, it took care of lots of math and planning that, had I done by hand, I may have messed up. Something like this may seem overwhelming, but truly, if you can text message or email someone, you can use this!

Once you have a handle on these tools, the sky’s the limit. For example, we have combined Google Sheets, Zapier, ChatGPT, and Google Docs with a Zap in Zapier. That integration allows us to put all of our core information about an auction into a spreadsheet. Zapier sees we have added a new line, and it parses out specific data and feeds it to ChatGPT, asking it to create ad copy and descriptions for the auction and output them to

To wrap this up, I promised it would be cheap and easy. So far, I have outlined the easy part. As for cheap, there are free versions of both of the tools we have discussed, and many other applications have free versions to get started, which may even be free forever based on your size. However, to get the level of integration I discussed in the last section, you need to invest some money. The monthly fee for Zapier for the level of integration I have talked about here is $19.99 per month, and the cost for ChatGPT Plus, which is required to integrate ChatGPT with external applications, is $20 per month. Nevertheless, these costs are reasonable and are outweighed by the significant benefits that automation and AI can bring to your auction business.

One final thing.  I am really bad at spelling and punctuation.  So I had ChatGPT review this article for me and clean it up.

The Lost Year: Back to Work

2015 was tough just no getting around it.  I started the year working with an amazing team as the CTO of a company I really believed in and the COO of the company that was supposed to be my future.  By the end of 2015, I had been through 3 jobs (all of my own choosing), I had spent most of the year just trying to find out what my employers really expected of me and honestly never getting an answer.  I don’t know if I can explain in words what it is like to go from the top of your game with people counting on you to make all the right decisions to people not even caring if you showed up to work.

But for me, it was a combination of things.  For the first time ever I really experience depression.  Having grown up with parent’s who deal with it and my wife who has made huge progress in her own mental health this was a shock to the system.  But I found out that it is something that I can cope with when presented with it and push through so that was a win.  Anxiety was not new to me.  Starting in early 2014 when a critical project refused to go right no matter what I did I started having mild anxiety attacks and they really screwed with me.  Being depressed is one thing but feeling totally out of control and on edge is a whole other thing that I was not really equipped to deal with.  But through luck, hiking, and lots of time to let my mind and body disconnect from years of stress that I had never dealt with the anxiety slipped away and for now has become dormant.  However, the hardest part was the self-doubt and that compounded both the depression and the anxiety.

After years of winning and moving forward, I had started to face failure no matter how hard I tried in my mid-30s.  Let me tell you that is a tough time to face failure with 3 kids, a mortgage and staff counting on you not to fuck up.  So when I jumped from a CTO/COO role to just being a cog in a big company I did so with plans to do more big things and get back on the winning path.  Roughly a year later that had not happened.  For about six months I had really been wondering if I had what it took to get back on the horse and do big things again.  I considered a few things, start back from scratch and become the best network engineer I could be and downsize my expectations for my future.  Honestly, that had lots of upsides and no matter how hard I try I would never be as good as most of my friends and engineers I look up to but I could do what I was good at which if fixing broken networks.  Option 2 was to find a nice safe role where I was where I consistently bang out what was expected of me and hopefully retire in 30 years but there was lots of stuff wrong with that plan so I pretty much said screw that from day one.  I am a lot of things but I am not lazy and willing to lay down and die.  If I am going to go out it will be swinging even it is failing my CCIE for the 400th time if that is even possible.  The final and most challenging (thus most likely for me to choose) was to go find a challenge that was bigger than my experience but allowed me to use my strengths.  If you are reading this you probably already know what I chose.

Just short of a year on from the decision to take on a Sr. Director of Operations role things are still humming along.  I write this hoping others see it and know that they are not alone when it feels like it is all coming unglued and years of work is slipping away.  For me, it took a year of soul-searching and unexpected downtime followed by doubling down.  Just remember to keep moving forward.

#WhoIS is BACK!

WOW it has been a long time.  It has taken life and career changes to get me back to the point that I have been able to really think about picking this up again.  I have had amazing feedback from the original audience and I am hoping to do even better for you al this time.

In the first season amazing guests in: Read more

A Few Easy Steps: Cisco Switch, Setup IP Device Tracking

In this session of A Few Easy Steps, we will be setting up IP Device Tracking on a Cisco IOS Switch. In General this will work on any Cisco IOS switch.  Session Prerequisites:

  • You have terminal or console access to your Cisco device.

Session Assumptions:

  • You have host devices connected to your switch

Our goals of this session are:

  • Globally enable IP Device Tracking
  • Setup all ports for IP Device Tracking
  • Show output of IP Device Tracking All Command

Read more