A Week in Chicago That Changed the Course of Our Lives
Earlier this year, Aaron and I stayed in Chicago for almost a week. The last time we were in the city was when we took a visit to see our long-time friend, Jimmy, who showed us both that awesome Italian grocery store, Eataly and the amazing Thorne Miniatures installation at the Art Institute of Chicago. (We had hoped to see him during this trip but, sadly, we didn’t give him enough notice as we couldn’t nail down the dates until the last minute. That meant while we were in his backyard, he was on the other side of the globe, having flown off to Madrid, Spain, I believe it was, on a spur-of-the-moment vacation to relax, tour glorious old cathedrals, and experience the local culture.)
It seems safe to say that it was probably one of the most important trips we’ve ever taken, the ramifications of which will be felt in ways that are difficult to calculate but that will no doubt reverberate for the remainder of our lives. While nearly all of our time was spent in meetings, working from the hotel, or touring real estate to give us a better idea of how we might make the city home if we end up living here for an 18-to-24-month stop-over in Illinois en route to relocating to the West Coast – something I briefly mentioned in the post on looking at office space in Southern California and that has to do, specifically, with the process of us having kids – two other things occurred.
- We came up with a plan to divest all of our operating assets, and intellectual property, related to the letterman jacket and letterman jacket award industries as part of our decision to reorder our entire careers around the asset management firm.
- We attended an incredibly helpful gestational surrogacy conference that provided us with the opportunity to sit in on panels with physicians, attorneys, and other specialists. These experts walked us through the process of having children by laying out a comprehensive roadmap of the surrogacy journey, and allowed us to hear from other couples who have built their families through surrogacy, speak with children (now adults) who had been born through surrogacy, and have question-and-answer sessions with women who had given the gift of surrogacy to others in the past. It was eye-opening in ways we didn’t anticipate but that deserves its own post in the future as we share that part of our lives with you.
During our time in the city, we called the Langham Hotel on the Chicago River home. We decided to give it a try because the location was convenient for our business needs, we had heard incredible things about it after it was named the best hotel in the United States last year, and we were thrilled with our experience when staying in the Langham Hotel in Pasadena several years ago. It turned out to be a great decision. The hotel itself is amazing but the staff really make it shine. It’s hard to describe but it was a deep competency in even the small things. They made everything easy, letting us focus on our work. From allowing us to use the boardroom on short notice and for as long as we needed (in fact, there was only a single day during the trip where they couldn’t accommodate us due to what I believe was a corporate pre-booking, in which case we were able to use the Club Lounge) to helping us gift wrap presents for our nieces and nephews, they made it possible for us stay productive. Whenever we needed to go somewhere, the car was waiting for us at the front of the building. If I needed a stack of stationary to take notes during long phone calls, problem solved. Those things add up and came together to to make it something special.
The first night, nearly everything was closed – turns out to be the story of this trip as by the time we were finished with work, few things were open – but we decided to walk around the city. It was great to see it like this. I understand why people take such pride in it.
My favorite part of the hotel was definitely the Club Lounge. The views were fantastic, the staff was always available to help, and you could be left alone to work in peace for hours at a time. There were days when I’d grab a stack of annual reports from the room, get a cup of coffee, and sit at one of the tables with my pen and highlighter, reading. They also had these ridiculously large, great-tasting glazed donuts for breakfast but the downside of that was they felt so indulgent you couldn’t help but skip lunch to make up for the nutritional sacrifice. Still, they were worth it. I get the feeling the food in this city is probably really good.
Speaking of which, we made a point to stop by Giordano’s because my brother kept urging us to indulge in one of their deep dish pizzas, which he loves.
The only bad part of the trip is that we couldn’t really enjoy much of the city because time didn’t permit us to do anything other than stick to our agenda. There were a few brief windows of time when we were able to take breaks and visit the Magnificent Mile. On one of these outings, we picked up a few things at Brooks Brothers because they were having a huge sale. We also managed to get a few small gifts elsewhere. 
Aaron and I have a lot to decide, and many of the decisions we’re facing will make sense when we start explaining the surrogacy process. For example, do we keep the house in Missouri? What does a person even do with multiple houses? We know lots of people who have them, and who seem to enjoy the convenience, but he and I prefer simplicity. Maybe that will change as we get older and have kids; pick up and go spend the summers near both grandmas and grandpas as we can work from nearly anywhere thanks to the nature of capital allocation. Still, it’s not something towards which we are drawn.
Regardless of whether a combination of favorable political laws and fate end up combining to result in us becoming residents for a couple of years, we end up having a layover somewhere else, or we go directly to California, we understand the reasons so many people love Chicago.
Reader Comments (30)
Comments are presented chronologically, with replies indented beneath the comments to which they respond.























Gilvus
October 8, 2017
Whenever you're ready...
I'm in the final stretch for studying for my licensing exam. Learning the history of the Newport-Inglewood Fault is making me irrationally worried for your future hypothetical safety.
Earthquakes. Earthquakes everywhere. Maybe you should live ABOVE Newport in a house suspended by drones. Or like that old guy in Pixar's Up.
Steven
October 9, 2017
Replying to Gilvus
I could see living in California near the coast for the fun lifestyle - but might not be the best place to raise kids.
As an individual you are consciously taking the risk, but the kids don't get a choice!
Earthquakes aren't like Hurricanes, you dont get to leave a few days beforehand based on a weather alert.
joe pierson
October 9, 2017
Replying to Steven
If you have money it's the greatest place to live, otherwise one of the worse places for a family.
jk
October 10, 2017
Replying to joe pierson
bogus. I have lived there, still have family living there, and none have bars nor have i seen any bars on windows of houses except in the parts of town near pawn shops, liquour stores, etc. This is anecdotal but carries as much or more weight than the comment above. If you believe what you here these guys should have been riding around in an armored personnel carrier while in Chicago to be safe.
Brendan
October 11, 2017
Replying to jk
jk - haha yeah, it reminds me of a Bill Hicks bit on watching CNN go on about the world ending, and then looking out your own window and just hearing crickets.
Dheeraj
October 12, 2017
Replying to Brendan
JK why not monaco or Miami.. i remember you mentioned how you went back to home town after you graduated to live near family.. now that operati g assests are divested.. whats the criteria.. isnt Miami, and monaco same level of liberal and more tax advantage filled then California.. tl;dr surrogacy must not have been only criteria.
Joshua Kennon
October 12, 2017
Replying to Dheeraj
(Was this addressed to me? I ask because it certainly looks like it has to be but in the administration panel, it shows this question was posted by replying to a guest Disqus user named jk in a conversation with joe pierson. My comments are under my full name with my picture visible in the avatar.)
Between various comment threads over the past year, and e-mails to the blog inbox, some variation of this question has been asked enough times that I probably need to write a detailed response. I had promised to do so in the future but my schedule kept getting in the way. I'll try, at some point over the next week, to make a stand-alone blog post specifically talking about how we arrived at this point, how we approached the trade-off decisions, and the things we need to think about going forward over the next three to five years. Once the full picture of what we're facing is mapped out, I think it's safe to say that a lot of the things we are doing will make a lot more sense.
Jeff
October 13, 2017
Replying to Joshua Kennon
Personally, I'm betting the increase in potential customers in California offset much of the higher tax load.
Harry Ramsay
October 17, 2017
Replying to Joshua Kennon
Please do; I'm sure a lot of people would be quite interested, myself included. It's rare that a decision like this can actually be followed in (almost) real-time as it's not something that happens very often with friends and family, so normally the perspectives that people do actually read about - in biographies and the like - are purely retrospective (and even then, very often glossed over, so it might read "... and then he moved to Chicago.") Just my €0.02.
Joshua Kennon
November 9, 2017
Replying to Harry Ramsay
I haven't forgotten about this, I still plan on writing about our thought process. I haven't had a moment to give it the attention it deserves but it will get done as soon as I can.
joe pierson
October 11, 2017
Replying to jk
>but carries as much or more weight than the comment above
Ha, maybe, my friend just bought this house, I lived in Venice Beach for a few years....
https://www.zillow.com/homedetails/2131-W-29th-Pl-Los-Angeles-CA-90018/20591436_zpid/
LordSquidworth
October 9, 2017
Replying to Steven
I was a baby in the tub in the 1989 earthquake and I turned out fine...
Jeff
October 9, 2017
You went back to paper annual reports?
Joshua Kennon
October 9, 2017
Replying to Jeff
About 95% digital on iPad Pro these days but sometimes I feel nostalgic and grab the physical copy. Usually that happens if one shows up in the mail and I want to read it right at that moment. On that trip, I knew we were going to be in the car for awhile so I took a stack with me.
Mykrohan
October 17, 2017
Replying to Joshua Kennon
You can read in the car? I have NEVER been able to do that. My head starts spinning within a New York minute and I feel like I want to retch.
ChuckECheese
October 23, 2017
Replying to Joshua Kennon
Curious what app you use to read financial statements with on the iPad Pro. Tried out several pdf reader that just don't seem to work as well.
Steven
October 9, 2017
A photo of Tiffanys! 30% of your readers felt a warm glow seeing their investment dollars make a guest appearance:)
Do you have a startup date for your firm yet Josh?
Courtney Parks
October 9, 2017
Good Morning Joshua, glad to see you're up early. I'm glad you enjoyed your trip up to Chicago. I've only been there a few times myself but I've enjoyed it each and every time! I also see that you're reading the Steve Jobs biography. I count that in the top 100 books that anyone who wants to be successful should read not because it's telling you the magic of the Apple computer or how Jobs sold it, but tells you the story of a man who dealt with extreme setbacks and still managed to bounce back from them. I hope you enjoy the book and hope that you can give us some of the stuff that you've learned from it! Please enjoy the rest of your day!
Joshua Kennon
November 9, 2017
Replying to Courtney Parks
The Jobs biography was definitely worth the read. There are a lot of things he did that I think were entirely unnecessary that brought a lot of misery and destruction into his life. (One thing I did appreciate was his emphasis on brand packaging but that's a personal bias because I've had a bit of an obsession with it for most of my life, and even collect books on product packaging design awards. There's something romantic to me about a well-designed Coca-Cola bottle or the way different perfume and alcohol companies create stories behind their brands, which is a sort of material manifestation of the signaling theory concept I've discussed a few times in passing on the blog.)
As you can imagine, my notes and markups are extensive - practically ever page looks like this and I don't recall how many highlighters I went through during the notation. I basically ruined any value the book would have to an outside reader, as usually is the case. My summary notes, though, were that the takeaway lessons are:
1. Make the product as simple as possible for the user.
2. Provide end-to-end solutions so you control the entire experience.
3. Be on the cutting edge of technology.
4. Design is not veneer. Get to the soul of a product – what is its function? – then remove as many unnecessary things as possible.
5. Only focus on 3 strategic priorities at a time.
6. If something isn’t right, don’t just ignore it and say you’ll fix it later.
7. Everyone in the company is responsible for the mission.
8. All tasks should be completed in the absolute minimum number of steps.
9. You must impute your brand identity and values in everything you do down to the packaging. Your own physical appearance, furniture, the website, etc.
10. Never lose control of your company.
11. By reducing the places where inventory can pile up, you reduce inventory.
12. There must be zero tolerance for non-performance.
13. Get people to become an evangelical for your brand.
14. Put on a great show.
15. Use trademark, copyright, and patent laws to your advantage.
16. “Which ones do I tell my friends to buy?” – look at your product and service offerings through this lens.
17. Focus. Knowing what not to do is as important as deciding what to do.
18. Stop bureaucratic momentum.
19. Build a lasting company. One of the best innovations is how you organize your firm.
20. Great products, great marketing, great distribution.
21. Just because someone charms you does not mean they like or respect you.
22. Don’t be set up for failure.
23. Know when to raise capital.
24. Only work with “A” players.
The biggest takeaway I have, though, is this: If I had lived, and died, with a story identical to Steve Jobs, I would not have considered my life a "life well-lived". That's the highest standard I apply to myself and, though to paraphrase Benjamin Graham that criterion based upon adjectives are necessarily ambiguous - it's something I feel in the deepest part of my heart. Of course, from a purely selfish standpoint as consumers, his self-destruction was hugely beneficial to me, you, and everyone we know. From the book, and everything else I've heard or read, I suspect the smartest decision Steve Jobs ever made was marrying his wife. He married up. Then, again, maybe that was demonstrative of his genius, too.
https://uploads.disquscdn.com/images/c9b7badb5ca17d13c692d917ef9773f13e553bcca4e17dedb377b81f4e557f24.jpg
Mr.owenr
November 12, 2017
Replying to Joshua Kennon
A life well lived? Its a dark place knowing I never had the courage to do what i thought should be done and never having had the self-discipline to deny present happiness through entertainment to achieve anything else.
Mine was most definitely not a life well lived, and nothing can change that. But it was the right thing to do at the time.
Brian Tracy says "you are responsible" and Joshua Kennon says, "a life well lived." It makes me uncomfortable, its like the phrase "a life well lived" is the only thing that stuck out from that comment. I suppose it means when you're on your deathbed you can be happy because you look back and know that you lived a life well lived. But you sacrifice all your current happiness from here to there to do so.
What an unnerving feeling, this "a life well lived" phrase makes. or does Joshua mean that you accomplish your major and minor life goals and then you are rewarded with the title, a life well lived. But it would be arrogant to think you get to be the judge of the important things to accomplish in your life. That's why you have parents, preachers, teachers, bosses...but I am responsible so says Brian Tracy. I've done what these people have said to do but I wouldn't consider meeting their goals a life well lived, but they would so now I'm confused, what does this phrase "a life well lived" mean?
Its like when my grand mother was dying I was distraught because I had to work instead of go see her in the hospital. I did the right thing and put in the work hours, and fulfilled my responsibility to my authorities but I wouldn't consider it to have been a life well lived, a life well lived I would have been financially independent enough to go see her. But who am I kidding, if I had been strong enough to take a day off I would have ended up playing video games anyways and possibly still not get to see her.
My God this is incoherent. A life well lived indeed! There must be some mantra I can chant to make sure that happens from here on out, since you can't think about things as you are doing them. I still have one family member, and I don't want to screw this up not for me since I'm worthless but for them.
Brendan
October 10, 2017
That deep dish pizza photo had me ready to grab the next flight to Chicago to get the real thing; it's the last major US city that I haven't explored (other than the airports) so I'll have to fix that soon! I chuckled at your question of "What does a person even do with multiple houses?" From the experiences related to me by my father-in-law who has homes in Maine and Virginia, the answer is: "mostly worry about what to do with those multiple houses." But, from reading your writings over the years, I know Missouri means a lot to you and there's just something special about where your grew up that helps ground you; so having a second home to take an extended visit to might be very worthwhile especially once you have children.
Joshua Kennon
November 9, 2017
Replying to Brendan
I have a hunch that your comment might turn out to be true - I can see us worrying about what's going on with the property, which is a distraction. We'll probably end up selling the house because of that. Still, I find myself more than a little tempted to have it redesigned and make it the best version of itself. I'm not one to get particularly attached to real estate but I'm definitely fond of the place. Aaron and I bought it when we were 26 (I had to check the dates because I remember we started looking when we were 25 but the actual closing date happened in February, less than a month before the DJIA hit bottom at 6,547.05 on March 9th, 2009).
The thing that will probably get me to sell? Aaron and I keep asking ourselves, "If our family weren't here, would we keep the house, let alone return to visit?". The answer: no. This begs the question... shouldn't we be working on getting our family to relocate, too?
Mykrohan
October 13, 2017
I love Chicago, but watching what's been happening to it - and the state of Illinois in general - for the past few years just fills me with a heart-wrenching sadness.
Good to have you back with us, Joshua.
Joshua Kennon
November 9, 2017
Replying to Mykrohan
The things to which you allude - the crime, pension costs, and general political troubles (I'm assuming given the well-publicized nature of them but I could be wrong) - definitely are factoring into our decision but everyone we know who has lived in, or presently lives in, Chicago assures us that it has practically no impact on their day-to-day life, particularly because if we were to take a layover in this city for a few years, the areas in which we would live and work are fundamentally different; most likely, places like The Gold Coast, Streeterville, or somewhere up in there.
On the other hand, compared to California, we expect Illinois will end up being much more attractive from a tax perspective (though there was a crazy proposal last year, I think it was, where some members of the state government wanted to try and get the voters to approve a constitutional amendment allowing an 11+% pass-through rate on limited liability companies, meaning small businesses would have paid far, far more than multi-billion dollar corporations).
it's funny what incentives do. If Washington state had modern gestational surrogacy laws that protected families and donors the same way Illinois and California do, we'd have relocated to Seattle for 3-5 years while the kids were being born. It'd have been such an easy decision. We could easily built the asset management business from there, our state income tax burden on pass-through entities would have been 0%, giving us a huge advantage, and it's a beautiful natural environment.
Kandice
October 29, 2017
So glad you're posting again! You do sound busy, with lots of things up in the air. Best wishes on the surrogacy planning, family planning, firm arrangements, and deciding where and when to set down roots. Just remember to take a few quiet moments for yourselves and each other.
Joshua Kennon
November 9, 2017
Replying to Kandice
Thank you for the best wishes! We're excited about everything that is happening (and you're right about needing to take a few quiet moments for ourselves and each other - we've been trying but it's something we have to consciously decide to do because the work is non-stop at this stage, which is a great problem to have). Freeing up our night and weekend time was a huge motivation in my decision to resign after nearly seventeen years from About.com yesterday and to sell our ownership in our letterman jacket awards business recently.
We've been talking about how much of the gestational surrogacy journey we want to share on the blog because it really is an amazing process and, although we'll obviously keep certain things private to protect everyone involved, providing a roadmap as we go through it could be a really interesting thing for people to see and experience with us. If it simplifies and makes the whole thing approachable, helping couples who otherwise might think it's too overwhelming, that would be a tremendously positive thing for the world. I've benefited so much from people being open and sharing knowledge so I'd like to keep paying that forward.
Smitty
November 7, 2017
I highly recommend Palos Verdes Estates, if you aren't already considering it. I grew up there. A true oasis in the craziness that is SoCal.
Joshua Kennon
November 9, 2017
Replying to Smitty
Thanks for the suggestion. We liked it a lot when we (briefly) drove through a few years ago and it keeps coming up in conversations so we'll definitely need to take a closer look at it.
Joshua Kennon
November 9, 2017
The gestational surrogacy journey is both incredible and fascinating at the same time. As I mentioned in another comment I left a bit ago elsewhere on this page, Aaron and I are seriously considering sharing much of the journey with the blog community (to the extent that the privacy of everyone involved can be protected, of course) so those who want to know how it works can learn about the process, experiencing it with us. Given the close-knit nature of the community, it might also offer a chance to let people ask questions they wouldn't be comfortable asking otherwise.
Mr.owenr
November 13, 2017
Replying to Joshua Kennon
That's some epic sci-fi crap dude. To think that more people who want children can have them makes me happy. Mind is blown.