Walks with Lenny

As one can see from any one of my prior reviews, I believe in being candid, open and honest when sharing my experience with others.
Having said that, I am extremely selective when it comes to my dog, Ossie. And even more so when I have to trust a total stranger to come into my home unsupervised or monitored and extend that to entrusting them with my dog.
I met Lenny on the very first day that I got Ossie. He was only 3-​months old at the time and I made a stop in the local dog park. I met several other local dog walkers that week and was not confident in the level of care and service that they would provide. Lenny is passionate about his commitment to the animals. He explained to me his process for scheduling, the timing of walks, sends text updates and even went so far as to clean up his «mistakes» when it occurred. Which, by the way, is a rare occurrence for Os. For me, I’d rather have someone who is committed to taking Ossie out during the day in the middle of a «polar vortex», blizzards, thunderstorms and extreme heat waves than someone who would give me a litany of excuses as to why they aren’t able to walk him. Like all dog walkers that service the area, he has help to cover all of the animals within the time frame (s) agreed with each owner. Let’s face it, every dog needs to be walked mid-​day and it is humanly impossible to walk them ALL at the same time. I have no issue with other members of his team walking Ossie because they demonstrate the same level of commitment and care for the animals. It is because of Lenny and his doggie daycare, that I decided to remain in the area. I know that his level of care can’t be replicated or found in another dog-​walker. For new pet owners below are some highlights and what you can anticipate:
Introduction: usually in-​person introduction so that you can meet him and he can meet your dog. That’s standard and who would want a strange business owner that they’ve never met in their home anyway?
Scheduling: via text message. If there is a change in schedule, advance notice is preferred but emergencies do come up. I try to give at least 24-​hours so that another dog can be slotted in.
Unit access: I’ve never had a problem because each of the buildings that I lived in, the concierge are familiar with Lenny and his helpers. If you set them up with «key access» then the doorman does not have to call for permission to grant them access. It makes it much easier for them too!
Walk updates: Usually a text message letting me know how Os is doing. I get an occasional photo of Ossie which always makes me smile. Updates are also sent when or if he is out of town or sick (which is incredibly rare. He was walking dogs after surgery!!) and his back-​up is filling in.
Overnight stays: You can chat with him directly. I’ve had a couple of instances where I needed Ossie walked outside of the normal hours and it was easy to set up. By the way, it is pretty standard to pay an extra fee for walks/​feeding on weekends and/​or late night.
I’ve been a customer for the past 3-​years and would absolutely recommend Lenny. Hands down the best in the area!

I have to say our experience is very similar to the Apr-​14 post below. We used Walks with Lenny when we first moved to Chicago, not a lot, but enough times to write the review. For a while things went fairly well — walks were on time, I’m sure our dog was in good hands, receive an occasional creepy selfie of Lenny with our dog, etc. However, one day we had requested a walk and feeding at 6pm because we were not going to be home until later that night. I received a call from our front desk saying some other company (who we did not know nor ever met) was asking them for the key to our place — at 4:30pm (our dog was still a puppy at the time and a few hours difference in feeding/​peeing can make a difference)!!! I texted Lenny to see what was going on and he said the other dog walker was sick and he couldnt do the walk so just sent over someone who lived nearby who never met us or Brutus, nor did he tell me that was plan. He was also unsure why the person showed up so early. I proceeded to have a phone conversation with Lenny in which he got defensive and annoyed with me for asking him to explain the situation. At the end of the conversation he begrudgingly agreed to go back and take our dog at the scheduled time and that he wouldnt take payment b/​c of the mixup — he proceeded to take the check anyway, not that I care but I did find it funny. Anyway, that was the last time we used Walks with Lenny. In summary, things are fine with Walks with Lenny until something happens where you question the situation or their handling of the situation. At that point, prepare for an argument. That was our experience anyway.

Lenny is a first class caregiver to our dog. It is very difficult to trust someone to not only enter your home, but to let them be in charge of someone you love so much. I love my dog like she is my very own birth child. It is obvious to us that Lenny loves our dog — as well as the many other dogs he walks. Our sweet girl runs (or drags me) to see Lenny when he is in the building and greets him with plenty of kisses and a waggly tail.
It brings me great joy to see how much she truly loves Lenny and that it is mutual. We’ve even adopted calling him «Uncle Lenny» because of how great he takes care of her.
He will go above and beyond for your furry baby without even asking him. One day, Lenny went to walk her and our air conditioner stopped working during the middle of a hot day. He called and texted my husband and I immediately, took her out of the hot apartment, gave her plenty of liquids, and kept her in a cooler place until maintenance fixed the air conditioner. Lenny only put our dog back in the apartment after it went back to a safe temperature. Not only did he do all of this, but he even went back to check on her an hour after everything was fixed to make sure she was ok. Your dog is in the best hands with Lenny. If it weren’t for him, who knows what could have happened that day.
I strongly recommend Walks With Lenny for dog-​walking and boarding services. He is absolutely fabulous and is truly passionate about your pet’s happiness and well-​being.

When I first met Lenny, I was excited by his energy and love for our four-​legged friends, and don’t get me wrong with the 1 star – he does love them. However his lack of respect and customer service are going to do him in.
I believe in starting with positives so let’s start with what I liked.. .
Walks with Lenny does not have a weekly walking minimum. This was perfect for our schedules and budget. Lenny was great at messaging us on Sunday to ask if we needed any services for the week.
Jackie was the BEST dog walker – she communicated really nicely and told us when she arrived and left our home. She was wonderful.
On to the not-​so-​good.. .
When I first met Lenny, what I liked about his business is that he assured me that there would only be one dog walker (himself) and on occasion (if he was tied up or on vacation) one other assistant. He clearly stated this is what sets Walks with Lenny apart from other dog walking businesses: «You would always have the same person. You’re not going to have a different person walking into your home.» Why is it that Lenny never entered our home? And that we had FOUR DIFFERENT walkers enter our home? Every time someone entered, we received another call to give permission to the new walker whom we never met. One other person I get, but FOUR?!
The other thing I did not appreciate about Lenny was the lack of customer service and respect he had. It always seemed that Lenny was never at fault and he would use A LOT OF CAPS to get his point across, which just comes off as though you are yelling/​trying to make a point/​rude.
Example.. .
Our last encounter was not a pleasant one. We were out-​of-​town and hired Lenny to do a day walk while our friend who was home-​sitting was at work. I requested the walker be there between 11 a.m. and 1 p.m. So I found it surprising when Lenny messages me at 1:45 p.m. saying that the (new) walker was having issues getting into our place. The two keys that were given to her were not working. We called our front desk and they assured us that she was able to get in on the second key, so why Lenny reached out? I am not sure.
I am not an innocent party.. .
I was beyond frustrated with Lenny because of the way he replied to me after I stated that no one had ever had a problem getting in our door. He replied with, «I understand that. But we are having one NOW.» **Mind you, the walker was already in after getting the 2^nd key**I asked Lenny to talk nicely please and ask the dog walker to go to the front desk for help ASAP because a) my dog should have been walked maximum 45 minutes ago and he still didn’t address the issue, and cap letters via text, email or review are yelling. He then proceeded to tell me the problem of the 2^nd key and I asked him to please stop arguing with me.
This wasn’t the first time we had a conversation like this.. .
I just never spoke up about his rude texts/​manners. I regret I never did because maybe it wouldn’t have gone this far – I blame the wine tasting :).
The outcome.. .
Lenny then replies back with the following text which can be see in the photos section. If you can’t see it here is what he said, «You know what Vanessa? I am NOT arguing with you. I am rebutting your insinuation she wasn’t smart enough to go downstairs and ask for help. Now, Lady will be walked today FREE of charge but I/​we are not walking her again after today.» And as you can see, I was perfectly okay with that.
Obviously, Lenny does not need customers nor does he care to keep them on. That’s not good customer service. By the way, this was our FIRST and ONLY (I am yelling: P) confrontation.
Since then (4÷26÷14), we have hired a new dog walker and they have entered our place twice with no problems, we have received photos and texts for when they go, and we have met the other dog walker who would possibly enter our home.
**FYI – I apologize as I did not proof read this**

If you ask ANYONE, I am highly obsessed with my dog, Zeus and would never consider leaving him with just ANYONE! However, Lenny is the kindest individual I have met in a really long time. His love for animals is really apparent. He is amazing to his employees and everyone he meets (humans and furry children). He is a kind soul and could watch or walk Zeus anytime:)

Walks with Lenny is the best service ever. He takes such good care of our two dogs. We hate being away from them, but Lenny makes use feel at ease. We always knows they love Lenny because from the moment he walks in the door the dogs are kissing and jumping for him. Lenny loves what he does and it shows. Sometimes I think our dogs would rather live with him… lol.